CAS No. :	17191-44-5
Formula :	C₁₄H₁₇NO₄
M.W :	263.29
SMILES Code :	O=C(O)C1(CCCC1)NC(OCC2=CC=CC=C2)=O
MDL No. :	MFCD02094399
InChI Key :	IXXMJXGMYKDTRQ-UHFFFAOYSA-N
Pubchem ID :	1512635

Safety of Cbz-Cyclo-Leu-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Cbz-Cyclo-Leu-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 17191-44-5 ]

[ 17191-44-5 ] Synthesis Path-Downstream 1~50

1
[ 949-67-7 ]
[ 17191-44-5 ]
[ 101813-77-8 ]

References: [1]Journal of the Chemical Society,1962,p. 4601 - 4607.

2
[ 17191-44-5 ]
[ 17191-51-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239.

3
[ 501-53-1 ]
[ 52-52-8 ]
[ 17191-44-5 ]

Yield	Reaction Conditions	Operation in experiment
78%		To a solution of 1-aminocyclopentanecarboxylic acid (3.0 g, 23.2 mmol) in 1:1 dioxane/water (60 mL), was slowly added Na2CO3 (12.3 g, 116 mmol) followed by benzyl chloroformate (3.6 mL, 25.5 mmol) and the mixture stirred overnight at RT. The reaction mixture was carefully acidified to pH=2 with 1M HCl then extracted with EtOAc (330 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo to leave a pale yellow oil. LCMS and NMR showed the crude product to be a mixture of desired product and corresponding benzyl ester. The crude product was dissolved in 1:1 THF/water (60 mL) and treated with lithium hydroxide (2.67 g, 116 mmol). The mixture was stirred at RT overnight then washed with Et2O (330 mL), acidified to pH=2 and extracted with EtOAc (3*30 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound (4.76 g, 78%). LCMS: m/z 264 [M+H]+.
78%		To a solution of 1-aminocyclopentanecarboxylic acid (3.0 g, 23.2 mmol) in 1 :1 dioxane / water (60 ml), was slowly added Na2CO3 (12.3 g, 116 mmol) followed by benzyl chloroformate (3.6 ml, 25.5 mmol) and the mixture stirred overnight at RT. The reaction mixture was carefully acidified to pH 2 with 1 M HCI then extracted with EtOAc (3 x 30 ml). The combined organic extracts were washed with brine (30 ml), dried (MgSO4), filtered and concentrated in vacuo to leave a pale yellow oil. LCMS and NMR showed the crude product to be a mixture of desired product and corresponding benzyl ester. The crude product was dissolved in 1 :1 THF / water (60 ml) and treated with lithium hydroxide (2.67 g, 116 mmol). The mixture was stirred at RT over night then washed with Et2O (3 x 30 ml), acidified to pH 2 and extracted with EtOAc (3 x 30 ml). The combined organic extracts were washed with brine (30 ml), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound (4.76 g, 78%). LCMS: m/z 264 [M+H]+.
62%	With sodium carbonate; In 1,4-dioxane; water; at 0 - 20℃;	A solution of benzyl chloroformate (0.290 g, 1.1 mmol) in dioxane (2.5 cm3) was added dropwise to a solution of 1 -aminocyclopentanecarboxylic acid (Fluka) (0.2 g, 1.54 mmol) and sodium carbonate (0.490 g, 4.64 mmol) in water (5 cm3) at 0 C. Stirring was continued at room temperature overnight and the reaction mixture washed with ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate, dried (Na2SO4), filtered and the solvent removed to afford carbamate 21 (0.253 g, 62%) as an oil which solidified on standing. Carbamate 21 was shown to be a 70:30 mixture of conformers by 1H NMR analysis (the ratio was estimated from the integration of the resonances at delta 5.31 and 7.29-7.40, assigned to the N-H protons of the major and minor conformers, respectively): mp 70-80 C (lit.1 82-86 C, ethyl acetate, petroleum ether); SH (400 MHz; CDCl3; Me4Si) 1.83 (4H, br s, 2 x cyclopentyl-H2), 2.04 (2H, br s, cyclopentyl-H2), 2.20-2.40 (2H, m, cyclopentyl- H2), 5.13 (2H, br s, OCH2Ph), 5.31 (0.7eta, br s, N-H) and 7.29-7.40 (5.3H, m, Ph and N-H*); deltac (100 MHz; CDCl3) 24.6 (CH2, cyclopentyl-C), 37.5 (CH2, cyclopentyl-C),' denotes resonance assigned to minor conformer. <n="31"/>66.0 (quat., cyclopentyl-C), 66.8 (CH2, OCH2Ph), 128.0 (CH, Ph), 128.1 (CH, Ph), 128.4 (CH, Ph), 136.1 (quat, Ph), 155.8 (quat., NCO2) and 179.5 (quat., CO2H).

62%	With sodium carbonate; In 1,4-dioxane; water; at 0 - 20℃;	N-Benzyloxycarbonyl-1-aminocyclopentane-1-carboxylic acid 21 A solution of benzyl CHLOROFORMATE (0.290 g, 1.1 mmol) in dioxane (2.5 CM3) was added dropwise to a solution of L-AMINOCYCLOPENTANECARBOXYLIC acid (Fluka) (0.2 g, 1.54 mmol) and sodium carbonate (0.490 g, 4.64 mmol) in water (5 CM3) at 0 C. Stirring was continued at room temperature overnight and the reaction mixture washed with ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate, dried (NA2S04), filtered and the solvent removed to afford carbamate 21 (0.253 g, 62%) as an oil which solidified on standing. Carbamate 21 was shown to be a 70: 30 mixture of conformers by 1H NMR analysis (the ratio was estimated from the integration of the resonances at No. 5.31 and 7.29-7. 40, assigned to the N-H protons of the major and minor conformers, respectively): mp 70-80 C (lit. l 82-86 C, ethyl acetate, petroleum ether); IH (400 MHz; CDC13 ; Me4Si) 1.83 (4H, br s, 2 x CYCLOPENTYL-H2), 2.04 (2H, br s, cyclopentyl-H2), 2.20-2. 40 (2H, M, cyclopentyl- H2), 5.13 (2H, br s, OCH2Ph), 5.31 (0.7H, br s, N-H) and 7.29-7. 40 (5.3H, M, Ph and N-H*) ; DC (100 MHz; CDC13) 24.6 (CH2, cyclopentyl-C), 37.5 (CH2, cyclopentyl-C), 66.0 (quat. , cyclopentyl-C), 66.8 (CH2, OCH2PH), 128.0 (CH, Ph), 128.1 (CH, Ph), 128.4 (CH, Ph), 136.1 (quat, Ph), 155.8 (quat. , NC02) and 179.5 (quat. , CO2H).
62%	With sodium carbonate; In 1,4-dioxane; water; at 0 - 20℃;	N-Benzyloxycarbonyl-l-aminocyclopentane-l-carboxylic acid 21 A solution of benzyl chloroformate (0.290 g, 1.1 mmol) in dioxane (2.5 cm3) was added dropwise to a solution of l-aminocyclopentanecarboxylic acid (Fluka) (0.2 g, 1.54 mmol) and sodium carbonate (0.490 g, 4.64 mmol) in water (5 cm3) at 0 C. Stirring was continued at room temperature overnight and the reaction mixture washed with ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate, dried (Na2SC>4), filtered and the solvent removed to afford carbamate 21 (0.253 g, 62%) as an oil which solidified on standing. Carbamate 21 was shown to be a 70:30 mixture of conformers by NMR analysis (the ratio was estimated from the integration of the resonances at 6 5.31 and 7.29-7.40, assigned to the N-H protons of the major and minor conformers, respectively): mp 70-80 C (lit.1 82-86 C, ethyl acetate, petroleum ether); < (400 MHz; CDC; Me4Si) 1.83 (4H, br s, 2 x cyclopentyl-H2), 2.04 (2H, br s, cyclopentyl-H2), 2.20-2.40 (2H, m, cyclopenty[-H2), 5.13 (2H, br s, OCiPh), 5.31 (0.7H, br s, N-H) and 7.29-7.40 (5.3H, m, Ph and N-H*); <5fc (100 MHz; CDC13) 24.6 (CH2, cyclopentyl-C), 37.5 (CH2, cyclopentyl-C), 66.0 (quat., cyclopentyl-C), 66.8 (CH2) OCH2Ph), 128.0 (CH, Ph), 128.1 (CH, Ph), 128.4 (CH, Ph), 136.1 (quat, Ph), 155.8 (quat, NC02) and 179.5 (quat., C02H).

References: [1]Organic Process Research and Development,1998,vol. 2,p. 238 - 244.
[2]Patent: US2010/317865,2010,A1 .Location in patent: Page/Page column 14; 15.
[3]Patent: WO2009/106844,2009,A1 .Location in patent: Page/Page column 39.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 70 - 74.
[5]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 533 - 548.
[6]Patent: WO2008/63311,2008,A2 .Location in patent: Page/Page column 29-30.
[7]Patent: WO2005/23815,2005,A2 .Location in patent: Page/Page column 42-43.
[8]Patent: WO2015/13397,2015,A2 .Location in patent: Page/Page column 45-46.
[9]Journal of the Chemical Society,1962,p. 4601 - 4607.
[10]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540.

4
[ 17191-44-5 ]
[ 735247-38-8 ]
(R)-4-[(1-Benzyloxycarbonylamino-cyclopentanecarbonyl)-amino]-2-tert-butoxycarbonylamino-butyric acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 379 - 384.

5
[ 1013-88-3 ]
[ 17191-44-5 ]
[ 39687-95-1 ]
{2-[(1-Benzyloxycarbonylamino-cyclopentanecarbonyl)-amino]-2,2-diphenyl-acetylamino}-acetic acid methyl ester [ No CAS ]

References: [1]Synthesis,1998,p. 991 - 998.

6
[ 1013-88-3 ]
[ 17191-44-5 ]
[ 71015-20-8 ]
2-{2-[(1-Benzyloxycarbonylamino-cyclopentanecarbonyl)-amino]-2,2-diphenyl-acetylamino}-2-methyl-propionic acid methyl ester [ No CAS ]

References: [1]Synthesis,1998,p. 991 - 998.

7
[ 17191-44-5 ]
[ 60421-23-0 ]
[ 94999-60-7 ]

References: [1]Journal of the American Chemical Society,1997,vol. 119,p. 11807 - 11816.

9
[ 17191-44-5 ]
[ 101651-14-3 ]
Acetic acid (2S,3S)-3-[(1-benzyloxycarbonylamino-cyclopentanecarbonyl)-amino]-4-oxo-azetidin-2-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2051 - 2053.

10
[ 17191-44-5 ]
[ 221186-79-4 ]
(R)-1-{(S)-2-[(1-Benzyloxycarbonylamino-cyclopentanecarbonyl)-amino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

11
[ 17191-44-5 ]
1-(2-amino-3-phenyl-propionyl)-piperidine-2-carboxylic acid tert-butyl ester [ No CAS ]
1-{2-[(1-benzyloxycarbonylamino-cyclopentanecarbonyl)-amino]-3-phenyl-propionyl}-piperidine-2-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

12
[ 17191-44-5 ]
[ 2133-40-6 ]
[ 842120-66-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 533 - 548.

13
[ 17191-44-5 ]
[ 6011-14-9 ]
[1-(cyanomethyl-carbamoyl)-cyclopentyl]-carbamic acid benzyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7520 - 7534.

14
[ 17191-44-5 ]
benzyl (1-cyanocyclopentyl)carbamate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239.

15
[ 17191-44-5 ]
[ 940868-36-0 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239.

16
[ 17191-44-5 ]
[ 519032-32-7 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239.

17
[ 17191-44-5 ]
2-[(1-benzyloxycarbonylamino-cyclopentanecarboximidoyl)-aminooxy]-but-2-enedioic acid dimethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239.

18
[ 17191-44-5 ]
2-(1-benzyloxycarbonylamino-cyclopentyl)-5,6-dihydroxy-pyrimidine-4-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239.

19
[ 17191-44-5 ]
[ 519032-31-6 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239.

20
[ 17191-44-5 ]
(1-(((benzyloxy)carbonyl)amino)cyclopentane-1-carbonyl)-L-proline [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 533 - 548.

21
[ 17191-44-5 ]
1-{2-[(1-amino-cyclopentanecarbonyl)-amino]-3-phenyl-propionyl}-piperidine-2-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

22
[ 17191-44-5 ]
C₂₉H₄₀N₄O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

23
[ 17191-44-5 ]
C₂₉H₄₁N₅O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

24
[ 17191-44-5 ]
C₃₆H₄₆N₄O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

25
[ 17191-44-5 ]
C₃₆H₄₆N₄O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

26
[ 17191-44-5 ]
1-(2-[1-(7-benzyloxycarbonyl-2-tert-butoxycarbonylamino-heptanoylamino)-cyclopentanecarbonyl]-amino}-3-phenyl-propionyl)-piperidine-2-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

27
[ 17191-44-5 ]
1-((S)-2-[1-((S)-2-Amino-7-benzyloxycarbonyl-heptanoylamino)-cyclopentanecarbonyl]-amino}-3-phenyl-propionyl)-piperidine-2-carboxylic acid tert-butyl ester; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5777 - 5784.

28
[ 17191-44-5 ]
[ 14855-33-5 ]

References: [1]Journal of the American Chemical Society,1997,vol. 119,p. 11807 - 11816.

29
[ 17191-44-5 ]
[ 17193-28-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540.

30
[ 17191-44-5 ]
[ 17193-66-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540.

31
[ 17191-44-5 ]
[ 17193-46-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 5,p. 531 - 540.

32
[ 17191-44-5 ]
N-(1-Amino-cyclopentancarbonyl)-L-tyrosin-aethylester [ No CAS ]

References: [1]Journal of the Chemical Society,1962,p. 4601 - 4607.

33
[ 17191-44-5 ]
methyl (S)-2-methylpyrrolidine-2-carboxylate monohydrochloride [ No CAS ]
methyl N-benzyloxycarbonyl(cyclopentylglycyl)-L-2-methylprolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With 1-hydroxy-7-aza-benzotriazole; 2-chloro-1,3-dimethyl-2-imidazolinium hexafluorophosphate; triethylamine; In 1,2-dichloro-ethane; at 20℃; for 19.1667h;Heating / reflux;	Dry triethylamine (0.19 cm3, 1.4 mmol) was added dropwise to a solution of hydrochloride 10 (78 mg, 0.43 mmol), carboxylic acid 21 (0.15 g, 0.56 mmol) and 1- hydroxy-7-azabenzotriazole (Acros) (15 mg, 0.1 1 mmol) in dry 1 ,2-dichloroethane (24 cm3) under an atmosphere of nitrogen at room temperature, and the reaction mixture stirred for 10 min. 2-Chloro-l,3-dimethylimidazolidinium hexafluorophosphate (CIP) (Aldrich) (0.12 g, 0.43 mmol) was added and the resultant solution heated under reflux for 19 h, then washed successively with 10% aqueous hydrochloric acid (30 cm3) and saturated aqueous sodium hydrogen carbonate (30 cm3), dried (MgSO4), filtered and evaporated to dryness in vacuo. Purification of the resultant residue by flash column chromatography (60% ethyl acetate-hexane) yielded amide 22 (39 mg, 23%) as a white solid. Amide 22 was shown to exist as a 3:1 trans :cis mixture of carbamate conformers by 13C NMR analysis (the ratio was estimated from the relative intensities of the resonances at delta 154.1 and 155.7 assigned to the carbamate carbonyl-C atoms of the major and minor conformers, respectively): mp 200-203 0C; [alpha]D -54.5 (c 1.52 in CH2Cl2); vmax (filmycm"1 3432, 3239, 3042, 2953, 1736, 1712, 1627, 1540, 1455, 1417, 1439, 1374, 1282, 1256, 1216, 1194, 1171, 1156, 1136, 1100, 1081, 1042, 1020, 107, 953, 917, 876, 756 and 701 ; Sn (400 MHz, CDCl3) 1.33-1.53 (3H, br m, Proalpha-CH3), 1.62-2.20 (HH, m, Probeta-H2, Progamma-H2 and 7 x cyclopentyl-H), 2.59-2.71 (IH, br m, 1 x cyclopentyl-H), 3.31-3.42 (IH, br m, Prodelta-H4HB), 3.58-3.79 (4H, br m, OCH3 and Prodelta-HAH/?), 4.92-5.17 (3H, m, N-H and OCH2Ph) and 121-1 Al (5eta, s, Ph); deltac (100 MHz, CDCl3) 21.7 (CH3, Proalpha-CH3), 24. I* (CH2, cyclopentyl-C), 24.2 (CH2, cyclopentyl-C), 24.4 (CH2, Progamma-C), 24.5 (CH2, cyclopentyl-C), 36.4 (CH2, cyclopentyl-C), 37.1 (CH2, cyclopentyl-C), 37.2* (CH2, cyclopentyl-C), 37.7 (CH2, Probeta-C), 38.2* (CH2, cyclopentyl-C), 48.5 (CH2, Prodelta-C), 52.1 (CH3, OCH3), 66.6 (CH2, OCH2Ph), 66.9 (quat., Proalpha-C), 67.2 (quat., Glyalpha-C), 127.8 (CH, Ph), 128.2 (CH, Ph), 128.4 (CH, Ph), 136.6 (quat., Ph), 154.1 (quat., NCO2), 155.7* (quat., NCO2), 170.5 (quat., GIy-CO) and 174.7 (quat., CO2CH3); m/z (EI+) 388.1991 (M+. C2iH28N2O5 requires 388.1998).
23%		METHYL N-BENZYLOXYCARBOT YL CYCLOPENTYL-GLYCYL-L-2-NAETHYLPROLINATE 22 Dry triethylamine (0.19 cm3, 1.4 mmol) was added dropwise to a solution of hydrochloride 10 (78 mg, 0.43 mmol), carboxylic acid 21 (0.15 g, 0.56 mmol) and 1- hydroxy-7-azabenzotriazole (ACROS) (15 mg, 0.11 mmol) in dry 1,2-dichloroethane (24 CM3) under an atmosphere of nitrogen at room temperature, and the reaction mixture stirred for 10 min. 2-CHLORO-1, 3-dimethylimidazolidinium hexafluorophosphate (CIP) (Aldrich) (0.12 g, 0.43 mmol) was added and the resultant solution heated under reflux for 19 h, then washed successively with 10% aqueous hydrochloric acid (30 CM3) and saturated aqueous sodium hydrogen carbonate (30 CM3), dried (MgSO4), filtered and evaporated to dryness in vacuo. Purification of the resultant residue by flash column chromatography (60% ethyl acetate-hexane) yielded amide 22 (39 mg, 23%) as a white solid. Amide 22 was shown to exist as a 3: 1 trans : cis mixture of carbamate conformers by 13C NMR analysis (the ratio was estimated from the relative intensities of the resonances at 8 154.1 and 155.7 assigned to the carbamate carbonyl-C atoms of the major and minor conformers, respectively): mp 200-203 C ; [A] D-54. 5 (c 1.52 in CH2Cl2) ; vmax (film)/cm-1 3432, 3239,3042, 2953,1736, 1712,1627, 1540,1455, 1417,1439, 1374,1282, 1256,1216, 1194, 1171,1156, 1136,1100, 1081,1042, 1020,107, 953,917, 876,756 and 701; No.H (400 MHz, CDCl3) 1.33-1. 53 (3H, br M, Proa-CH3), 1.62-2. 20 (11H, M, PROP-H2, PROY-H2 and 7 x cyclopentyl-H), 2.59-2. 71 (1H, br M, 1 x cyclopentyl-H), 3.31-3. 42 (1H, br m, PRO6-HAHB), 3.58-3. 79 (4H, br M, OCH3 and PRO8-HAHB), 4.92-5. 17 (3H, M, N-H and OCH2Ph) and 7.27-7. 42 (5H, s, Ph); (100 MHz, CDCl3) 21.7 (CH3, PROA-CH3), * denotes resonance assigned to minor conformer. 24.1* (CH2, cyclopentyl-C), 24.2 (CH2, cyclopentyl-C), 24.4 (CH2, Proy-C), 24.5 (CH2, cyclopentyl-C), 36.4 (CH2, cyclopentyl-C), 37.1 (GHZ, cyclopentyl-C), 37.2* (CH2, cyclopentyl-C), 37.7 (CH2, PROP-C), 38.2* (CH2, cyclopentyl-C), 48.5 (CH2, Pro8-C), 52.1 (CH3, OCH3), 66.6 (CH2, OCH2Ph), 66.9 (quat. , PROA-C), 67.2 (quat. , GLYalpha-C), 127.8 (CH, Ph), 128.2 (CH, Ph), 128.4 (CH, Ph), 136.6 (QUAT., Ph), 154.1 (quat. , NCO2), 155.7* (quat. , NCO2), 170.5 (quat. , Gly-CO) and 174.7 (quat. , C02CH3) ; m/z (EI+) 388.1991 (M+. C2LH28N205 requires 388.1998).
23%	With 1-hydroxy-7-aza-benzotriazole; 2-chloro-1,3-dimethyl-2-imidazolinium hexafluorophosphate; triethylamine; In 1,2-dichloro-ethane; for 19h;Inert atmosphere; Reflux;	Methyl N~benzyloxycarbonyl cyclopentyl-glycyl-L-2-methylprolinate 22 Dry triethylamine (0.19 cm3, 1.4 mmol) was added dropwise to a solution of hydrochloride 10 (78 mg, 0.43 mmol), carboxylic acid 21 (0.15 g, 0.56 mmol) and 1 -hydroxy-7- azabenzotriazole (Acros) (15 mg, 0.11 mmol) in dry 1,2-dichloroethane (24 cm3) under an atmosphere of nitrogen at room temperature, and the reaction mixture stirred for 10 min. 2- Chloro-l,3-dimethylimidazolidinium hexafluorophosphate (CIP) (Aldrich) (0.12 g, 0.43 mmol) was added and the resultant solution heated under reflux for 19 h, then washed successively with 10% aqueous hydrochloric acid (30 cm3) and saturated aqueous sodium hydrogen carbonate (30 cm3), dried (MgS04), filtered and evaporated to dryness in vacuo. Purification of the resultant residue by flash column chromatography (60% ethyl acetate-hexane) yielded amide 22 (39 mg, 23%) as a white solid. Amide 22 was shown to exist as a 3:1 trans: cis mixture of carbamate conformers by l3C NMR analysis (the ratio was estimated from the relative intensities of the resonances at delta 154.1 and 155.7 assigned to the carbamate carbonyl-C atoms of the major and minor conformers, respectively): mp 200-203 C; [a]D -54.5 (c 1.52 in CH2C1 ); v,MX (film)/cm" 3432, 3239, 3042, 2953, 1736, 1712, 1627, 1540, 1455, 1417, 1439, 1374, 1282, 1256, 1216, 1194, 1171, 1156, 1136, 1100, 1081, 1042, 1020, 107, 953, 917, 876, 756 and 701; < (400 MHz, CDClj) 1.33-1.53 (3H, br m, Proa-C), 1.62-2.20 (11H, m, Prop-H2, Proy- and 7 x cyclopentyl-H), 2.59-2.71 (1H, br m, 1 x cyclopentyl-H), 3.31-3.42 (1H, br m, Pro5-HB), 3.58- 3.79 (4H, br m, OCH3 and Pro5-HA , 4.92-5.17 (3H, m, N-H and OCiPh) and 7.27-7.42 (5H, s, Ph); Sc (100 MHz, CDC13) 21.7 (CH3, Proa-CH3), 24.1* (C, cyclopentyl-C), 24.2 (CH2, cyclopentyl-C), 24.4 (CH2, Proy-C), 24.5 (CH2, cyclopentyl-C), 36.4 (CH2, cyclopentyl-C), 37.1 (CH2, cyclopentyl-C), 37.2* (CH2, cyclopentyl-C), 37.7 (CH2, RhoGammathetabeta-C), 38.2* (CH2, cyclopentyl- C), 48.5 (CH2, Pro6-C), 52.1 (CH3, OCH,), 66.6 (CH2j OCH2Ph), 66.9 (quat., Proct-C), 67.2 (quat., Glyc -C), 127.8 (CH, Ph), 128.2 (CH, Ph), 128.4 (CH, Ph), 136.6 (quat., Ph), 154.1 (quat., NC02), 155.7* (quat., NC02), 170.5 (quat., Gly-CO) and 174.7 (quat., C02CH3); m/z (EI+) 388.1991 (M+. C2,H28N205 requires 388.1998). * denotes resonance assigned to minor conformer.

References: [1]Patent: WO2008/63311,2008,A2 .Location in patent: Page/Page column 30.
[2]Patent: WO2005/23815,2005,A2 .Location in patent: Page/Page column 43-44.
[3]Patent: WO2015/13397,2015,A2 .Location in patent: Page/Page column 46.

34
[ 5048-82-8 ]
[ 17191-44-5 ]
[ 494854-35-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 40℃; for 48h;	l-[(benzyloxy)carbonyl]amino}cyclopentanecarboxylic acid was dissolved in DMF (0.2 M). HATU (1 eq.) and triethylamine (3 eq.) were added, followed by ethyl (2u)-3-(4-aminophenyl)acrylate (0.95 eq.). The resulting mixture was stirred for 48 h at 40 0C. DMF was evaporated, the resulting oil taken up in EPO <DP n="18"/>EtOAc and the solution washed with hydrochloric acid (3x, 1 M), water, a solution of saturated aqueous NaHCO3 (2x) and brine. Drying over sodium sulfate and evaporation gave an orange solid, which was purified by flash chromatography on silica gel using PE/EtOAc (2.5 : 1, containing 1% EtOH) as the eluant. The resulting solid was immediately dissolved in DCM (0.1 M) and triflic acid (5 eq.) was added dropwise at RT. After 5 min at RT, the red mixture was poured into an aqueous solution OfNaHCO3. The organic phase was separated, the aqueous phase was extracted with DCM (4x) and the combined organic phases dried over sodium sulfate. Evaporation gave the title compound as an off-white solid, which was used without further purification. 1H NMR (400 MHz, DMSO-fi?6, 300 K) delta 1.26 (t, J 7.1, 3H), 1.48-1.61 (m, 2H), 1.63-1.87 (m, 4H), 1.96-2.10 (m, 2H), 4.188 (q, J7.1 Hz, 2H), 6.53 (d, J 16.0, IH), 6.60-7.30 (bs, 3H), 7.59 (d, J 16.0, IH), 7.67 (d, J8.5, 2H), 7.76 (d, J8.5, 2H); MS (ES+) m/z 303 (M+H)+.
		Step 7; Ethyl (2E)-3 (4-{ [(1-aminocyclopentyl)carbonyl]amino}phenyl)acrylate; 1-[benzyloxy)carbonyl]amino}cyclopen(anecarboxylic acid was dissolved in DMF (0.2 M). HATU (1 eq.) and triethylamine (3 eq.) were added, followed by ethyl cinnamate (0.95 eq.). The resulting mixture was stirred for 48 h at 40 C. DMF was evaporated, the resulting oil taken up in EtOAc and the solution washed with HQ (3x, 1 M), water, a solution of saturated aqueous NaHC03 (2x) and brine. Drying over Na2SO4 and evaporation gave an orange solid, which was purified by flash chromatography on silica gel using PE/EtOAc (2.5 : 1. containing 1% EtOH) as the eluent The resulting solid was immediately dissolved in DCM (0,1 M) and triflic acid (5 eq.) was added dropwise at RT, After 5 mm at RT, the red mixture was poured into an aqueous solution of NaHCOj. The organic phase was separated, the aqueous phase was extracted with DCM (4x) and the combined organic phases dried over Na2SO4. Evaporation gave the title compound as an off-white solid, which was used without further purification.

References: [1]Patent: WO2007/29029,2007,A2 .Location in patent: Page/Page column 16-17.
[2]Patent: WO2006/29912,2006,A1 .Location in patent: Page/Page column 24.

35
[ 5048-82-8 ]
[ 17191-44-5 ]
C₂₅H₂₈N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 40℃; for 48h;	Example 11: (2E)-3-{4-[({l-[({14-[(trans)-2-fluorocyclohexyl]-6-isopropyl-3-methoxy-5,6,7,8- tctrahydroindolo[2,l -a] [2,5]bcnzodiazocin-l 1 -yl}carbonyl)amino] cyclopcntyl} carbonyl)amino]phcnyl}acrylic acid Step 1: ethyl (2E)-3-(4-{f(l-aminocvclopentyl)carbonylJamino}phenyl)acrylate trifluoroacetate l-[(benzyloxy)carbonyl]amino}cyclopentanecarboxylic acid was dissolved in DMF (0.2 M). HATU (1 eq) and triethylamine (3 eq) were added, followed by ethyl (2u)-3-(4-aminophenyl)acrylate (0.95 eq). The resulting mixture was stirred for 48 h at 40 0C. DMF was evaporated, the resulting oil taken up in EtOAc and the solution washed with aqueous HCl (IN), water, saturated aqueous NaHCO3 and brine. Drying over NaHSO4 and evaporation gave an orange solid, which was purified by flash chromatography on silica gel using PE/EtOAc (2.5 : 1, containing 1% EtOH) as the eluent. The resulting solid was dissolved at 0 0C with a 1 : 1 mixture of TFA:CH2C12, and the solution (0.1 M) was stirred for 2 h at RT. Evaporation gave a residue that was triturated with toluene to afford a solid that was used without further purification in the subsequent step. 1H NMR (400 MHz, DMSO-fi?6, 300 K) delta, 1.34 (t, J 6.9, 3H), 1.90- 2.12 (m, 4H), 2.50-2.65 (m, 4H), 4.15 (q, J6.9, 2H), 6.62 (d, J 16.0, 1 H), 7.69 (d, J 16.0, 1 H), 7.80 (br s, 2H), 8.35 (br s, 2H) 10.22 (s, IH); MS (ES+) m/z 303 (M+H)+.

References: [1]Patent: WO2007/54741,2007,A1 .Location in patent: Page/Page column 34.

36
[ 1367370-59-9 ]
[ 17191-44-5 ]
[ 1367370-13-5 ]

References: [1]Chemical Communications,2012,vol. 48,p. 3397 - 3399.

37
[ 17191-44-5 ]
[ 4089-07-0 ]
[ 101813-77-8 ]

References: [1]Organic Process Research and Development,1998,vol. 2,p. 238 - 244.

38
[ 17191-44-5 ]
N-[[1-[[(phenylmethoxy)carbonyl]amino]-1-cyclopentyl]carbonyl]-O-methyl-L-tyrosine ethyl ester [ No CAS ]

References: [1]Organic Process Research and Development,1998,vol. 2,p. 238 - 244.

39
N1-(1-(cycloheptylmethyl)piperidin-4-yl)benzene-1,2-diamine [ No CAS ]
[ 17191-44-5 ]
1-(1-(1-(cycloheptylmethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2-yl)cyclopentanamine hydrochloride salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%		To a solution of the product from Example lc (50 mg, 0.166 mmol) in methylene chloride (5 mL) was added N-Cbz-l-aminocyclopentanecarboxylic acid (50 mg, 0.190 mmol, prepared as described in Johnson et al, Org. Proc. Res. Dev. 1998, 2, 238), N-hydroxybenzotriazole (HOBT, 30 mg, 0.196 mmol), N-methylmorpholine (0.04 mL, 0.364 mmol), 4-dimethylaminopyridine (5 mg), and l-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (EDC, 64 mg, 0.335 mmol). The resulting mixture was stirred at room temperature for 36 h. After removal of solvent by rotary evaporation, the residue was dissolved in methylene chloride (10 mL) and washed with a saturated aqueous solution of NaHC03 (10 mL). The aqueous layer was extracted twice with additional methylene chloride (5 mL) and the combined organic layers were dried over Na2SC"4, filtered, and concentrated in vacuo. Without further purification, the residue was dissolved in acetic acid (1.5 mL) and stirred at 100 C for 72 h. The solution was cooled, concentrated, and partitioned between a saturated aqueous solution of NaHC03 (10 mL) and methylene chloride (10 mL). The layers were separated, and the aqueous layer was extracted with two additional portions of methylene chloride (10 mL). The organic layers were combined, dried over Na2S04, filtered, concentrated in vacuo, and purified by flash column chromatography (5 to 60% ethyl acetate in hexanes). The obtained oil was dissolved in ethyl acetate (5 mL). To this solution was added 10%> palladium on carbon (0.25 g) and the reaction was stirred under a hydrogen atmosphere using a balloon filled with hydrogen gas for 12 h at room temperature. After removal of catalyst by filtration through a pad of Celite, the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (0.4-5%) methanol in CH2C12 with 0.1% NH4OH) and converted to HCl salt to provide the title compound as a colorless solid (9.7 mg, 12%). LRMS (ES+) m/z for C25H39N4 [M+H]+ calc'd 395, found 395.

References: [1]Patent: WO2014/153529,2014,A1 .Location in patent: Page/Page column 68-69.

40
[ 17191-44-5 ]
methyl (S)-2-methylpyrrolidine-2-carboxylate monohydrochloride [ No CAS ]
[ 847952-39-0 ]

References: [1]Patent: WO2015/13397,2015,A2 .

41
[ 17191-44-5 ]
C₁₉H₃₅N₃O₄ [ No CAS ]
C₃₃H₅₀N₄O₇ [ No CAS ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 6343 - 6356.

42
[ 17191-44-5 ]
(E)-2-hydroxy-1-(methyl(oxo)(phenyl)-λ⁶-sulfaneylidene)guanidine [ No CAS ]
benzyl (1-(3-((methyl(oxo)(phenyl)-λ⁶-sulfanylidene)amino)-1,2,4-oxadiazol-5-yl)cyclopentyl)carbamate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 9187 - 9199.

43
[ 17191-44-5 ]
[ 76492-19-8 ]
C₃₃H₅₂N₄O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		General procedure: N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDCI·HCl, 1.00 equiv) and 1-hydroxybenzotriazole hydrate (HOBt·H2O, 1.20 equiv) were added to the stirred solution of carboxylic acid (1.00 equiv) in CH2Cl2 (0.2 M) at 0 C, and the mixture was stirred at 0 C for 30 min. Then, a solution of amine in CH2Cl2 (0.2 M) was dropped to the reaction mixture at 0 C. In the case that the amine was used as a HCl salt, N,N-diisopropylethylamine (DIPEA, 2.40 equiv) was added. The reaction mixture was gradually warmed to room temperature and stirred overnight. After removal of CH2Cl2, the residue was diluted with EtOAc and washed successively with 1 M HCl, water, 5% aqueous NaHCO3, and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to give a crude product, which was purified by flash column chromatography on silica gel.

References: [1]Tetrahedron Letters,2019,vol. 60.

44
[ 17191-44-5 ]
Boc-L-Leu-Ac5c-(L-Leu)3-OMe [ No CAS ]

References: [1]Tetrahedron Letters,2019,vol. 60.

45
[ 17191-44-5 ]
C₂₅H₄₆N₄O₅ [ No CAS ]

References: [1]Tetrahedron Letters,2019,vol. 60.

46
[ 17191-44-5 ]
Boc-L-Leu-Ac5c-(L-Leu)5-OMe [ No CAS ]

References: [1]Tetrahedron Letters,2019,vol. 60.

47
[ 17191-44-5 ]
H-L-Leu-Ac5c-(L-Leu)5-OMe [ No CAS ]

References: [1]Tetrahedron Letters,2019,vol. 60.

48
[ 17191-44-5 ]
C₃₅H₆₃N₅O₈ [ No CAS ]

References: [1]Tetrahedron Letters,2019,vol. 60.

49
[ 17191-44-5 ]
Boc-(L-Leu)3-Ac5c-(L-Leu)3-OMe [ No CAS ]

References: [1]Tetrahedron Letters,2019,vol. 60.

50
[ 17191-44-5 ]
H-(L-Leu)3-Ac5c-(L-Leu)3-OMe [ No CAS ]

References: [1]Tetrahedron Letters,2019,vol. 60.

Historical Records

Technical Information

• Halogenation • Heat of Combustion • Reactions of Amines

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CAS No.: 17191-44-5

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CAS No.: 17191-44-5

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Product Details of Cbz-Cyclo-Leu-OH

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Application In Synthesis of Cbz-Cyclo-Leu-OH

[ 17191-44-5 ] Synthesis Path-Downstream 1~50

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