117997-81-6|5-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid| Ambeed

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Quality Control of [ 117997-81-6 ] Purity: 97% SDS Specification

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Product Details of [ 117997-81-6 ]

CAS No. :	117997-81-6
Formula :	C₁₇H₂₃NO₆
M.W :	337.37
SMILES Code :	O=C(O)C(NC(OC(C)(C)C)=O)CCC(OCC1=CC=CC=C1)=O
MDL No. :	MFCD00798612
InChI Key :	AJDUMMXHVCMISJ-UHFFFAOYSA-N
Pubchem ID :	295483

Safety of [ 117997-81-6 ]

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

Application In Synthesis of [ 117997-81-6 ]

* 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 [ 117997-81-6 ]

[ 117997-81-6 ] Synthesis Path-Downstream 1~42

1
[ 117997-81-6 ]
2-[2-Amino-3-(diphenoxy-phosphoryloxy)-propionylamino]-methyl}-3-methyl-butyric acid benzyl ester; compound with trifluoro-acetic acid [ No CAS ]
[ 105751-09-5 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 1373 - 1376.

2
[ 117997-81-6 ]
[ 95656-84-1 ]

References: [1]Organic Letters,2014,vol. 16,p. 4228 - 4231.
[2]Journal of the Chemical Society. Chemical communications,1984,p. 1298 - 1299.

3
[ 117997-81-6 ]
[ 2050-92-2 ]
[ 118100-26-8 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 591 - 595.

4
[ 100-02-7 ]
[ 117997-81-6 ]
4-nitrophenyl γ-benzyl-N-tert-butoxycarbonylglutamate [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

5
[ 24424-99-5 ]
[ 29456-09-5 ]
[ 117997-81-6 ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.
[2]New Journal of Chemistry,2019,vol. 43,p. 12109 - 12117.

6
[ 117997-81-6 ]
lysine benzyl ester bis(trifluoroacetate) [ No CAS ]
N,N'-bis(tert-butoxycarbonyl-γ-benzylglutamyl)lysine benzyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

7
[ 117997-81-6 ]
N,N'-bis(phenylalanyl)ethylenediamine bis(trifluoroacetate) [ No CAS ]
[ 122262-04-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

8
[ 117997-81-6 ]
[ 104-15-4 ]
H-Glu(OBzl)-OH p-toluenesulfonic acid salt [ No CAS ]

References: [1]Synthetic Communications,2005,vol. 35,p. 1795 - 1802.

9
[ 93578-22-4 ]
[ 117997-81-6 ]
4-(6-allyl-benzo[1,3]dioxol-5-ylcarbamoyl)-4-<i>tert</i>-butoxycarbonylamino-butyric acid benzyl ester [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2004,vol. 39,p. 1059 - 1065.

10
[ 117997-81-6 ]
N,N'-bis(tert-butoxycarbonyl-γ-benzylglutamyl)ethylenediamine [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

11
[ 117997-81-6 ]
N,N'-bis(γ-benzylglutamyl)ethylenediamine bis(trifluoroacetate) [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

12
[ 117997-81-6 ]
N,N'-bis(tert-butoxycarbonylphenylalanyl-γ-benzylglutamyl)ethylenediamine [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

13
[ 117997-81-6 ]
N,N'-bis(γ-benzylglutamyl)lysine benzyl ester bis(trifluoroacetate) [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

14
[ 117997-81-6 ]
N,N'-bis(phenylalanyl-γ-benzylglutamyl)ethylenediamine bis(trifluoroacetate) [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

15
[ 117997-81-6 ]
N,N'-bis(γ-benzylglutamylphenylalanyl)ethylenediamine bis(trifluoroacetate) [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1765 - 1780.

16
[ 117997-81-6 ]
[ 105751-06-2 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 1373 - 1376.
[2]Tetrahedron Letters,1986,vol. 27,p. 1377 - 1380.

17
[ 117997-81-6 ]
[ 105751-11-9 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 1373 - 1376.

18
[ 117997-81-6 ]
[ 117997-60-1 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 591 - 595.

19
[ 117997-81-6 ]
[ 123540-70-5 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 591 - 595.

20
[ 117997-81-6 ]
[ 123540-71-6 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 591 - 595.

21
[ 117997-81-6 ]
[ 117997-61-2 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 591 - 595.

22
[ 117997-81-6 ]
[ 118100-27-9 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 591 - 595.

23
[ 117997-81-6 ]
[ 18807-74-4 ]
Boc-Glu(OBzl)-NH(CH₂)5-NH-Z [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 27h;	To a solution of <strong>[117997-81-6]Boc-Glu(OBzl)-OH</strong> (0.30 g, 0.90 mmol) and N-Z-1,5-pentanediamine hydrochloride (0.24 g, 0.90 mmol) in DMF (10 mL) at 0 C. were added NMM (0.10 mL, 0.90 mmol), HOBt (0.15 g, 0.99 mmol) and WSC (0.19 g, 0.99 mmol). Z is the protecting group benzyloxycarbonyl. The reaction mixture was stirred for 3 h at 0 C. and for 24 h at room temperature. After DMF was evaporated, the residue was solubilized in EtOAc and washed with citric acid (10%), NaHCO3 (5%), and brine. The organic phase was dried and evaporated to dryness. The residue was crystallized from Et2O/Pe (1:9, v/v): yield 0.47 g (94%); Rf (B) 0.94; HPLC K'=9.15; mp 141-143 C.; [α]20D+20.4; MH+ 556; 1H NMR (DMSO) δ 1.29-1.55 (m, 15 H), 2.18-2.25 (m, 4H), 2.96-3.20 (m, 4H), 4.53-5.34 (m, 5H), 7.11-7.29 (m, 10H).

References: [1]Patent: US2006/104907,2006,A1 .Location in patent: Page/Page column 7.

24
[ 5202-89-1 ]
[ 117997-81-6 ]
methyl 2-(5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanamido)-5-chlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		(i) Methyl 2-(5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanamido)-5-chlorobenzoateAfter adding 4.0 g (11.9 mmol) of DL-<strong>[117997-81-6]Boc-Glu(OBzl)-OH</strong> to acetonitrile, 2.9 g (35.6 mmol) of N-methyl imidazole and 2.7 g (14.2 mmol) of p-toluene sulfonyl chloride were added and stirring for 1 hour at 0 C. Subsequently, 2.2 g (11.9 mmol) of methyl 2-amino-5-chlorobenzoate was added, and the mixture was stirred at room temperature overnight. After concentration, the reaction mixture was diluted with ethyl acetate, and washed with water. After drying the resulting organic layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The crude product obtained was separated and purified by silica gel column chromatography to give 2.5 g of methyl 2-(5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanamido)-5-chlorobenzoate (yield 41%).1H-NMR (CDCl3) δ: 1.46 (9H, s), 1.95-2.15 (1H, m), 2.23-2.43 (1H, m), 2.49-2.62 (2H, m), 3.92 (3H, s), 4.26-4.45 (1H, m), 5.13 (2H, s), 5.35 (1H, d, J=8.2 Hz), 7.29-7.42 (5H, m), 7.49 (1H, dd, J=9.2, 2.6 Hz), 8.00 (1H, d, J=2.6 Hz), 8.69 (1H, d, J=9.2 Hz), 11.5 (1H, s).

References: [1]Patent: US2009/124620,2009,A1 .Location in patent: Page/Page column 46.

25
[ 4556-23-4 ]
[ 117997-81-6 ]
C₂₂H₂₆N₂O₅S [ No CAS ]

References: [1]Organic Letters,2010,vol. 12,p. 4716 - 4719.

26
[ 117997-81-6 ]
[ 62-53-3 ]
[ 126349-57-3 ]

Yield	Reaction Conditions	Operation in experiment
94%		To a stirred solution of Boc-L-glutamic acid 5-benzyl ester [4a] (41 g, 122 mmol) in anhydrous CH2Cl2 (45 ml) at O0C, was added during 15 minutes a solution of DCC (30.1 g, 146 mmol) in anhydrous CH2Cl2 (45 ml). The resulting white solid was sonicated. After that, anhydrous aniline was added dropwise to the reaction mixture over 10 minutes at O0C (11.1 ml, 122 mmol). The mixture was stirred at room temperature for 40 minutes and filtered through Celite to remove insoluble material. The resulting liquid was evaporated to dryness and chromatographically purified, yielding the desired product (47.2 g, 94%).1H-NMR (400 MHz, CDCl3): δ: 8.40 (br, IH, CONHPh), 7.43 (d, 2H, J=7.7 Hz, 2Ha), 7.28 (d, 2H, J=7.7 Hz, Hb), 7.20 (m, 5H, 5xHd), 7.02 (t, IH, J=7.4 Hz, Hc), 5.35 (d, IH, J=7.8 Hz, CHNHBoc), 5.04 (d, 2H, J=2.6 Hz, BnOCH2), 4.26 (sa, IH, CH2CHNHBoC), 2.60-2.52 (me, IH, IxOCOCH2CH2), 2.46-2.38 (me, IH, Ix OCOCH2CH2), 2.21-2.12 (me, IH, IxOCOCH2CH2), 1.99-1.90 (me, IH, Ix OCOCH2CH2), 1.40 (s, 9H, MS: Positive mode [M + Na]+ = 435.MS: Negative mode [M + 2 H2O - H]- = 447.
94%		Example 1 Preparation of intermediate [6a]: Benzyl 4-(tert-butoxycarbonylamino)-5-oxo-5-(phenylamino) pentanoate To a stirred solution of Boc-L-glutamic acid 5-benzyl ester [4a] (41 g, 122 mmol) in anhydrous CH2Cl2 (45 ml) at 0C, was added during 15 minutes a solution of DCC (30.1 g, 146 mmol) in anhydrous CH2Cl2 (45 ml). The resulting white solid was sonicated. After that, anhydrous aniline was added dropwise to the reaction mixture over 10 minutes at 0C (11.1 ml, 122 mmol). The mixture was stirred at room temperature for 40 minutes and filtered through Celite to remove insoluble material. The resulting liquid was evaporated to dryness and chromatographically purified, yielding the desired product (47.2 g, 94%). 1H-NNM (400 MHz, CDCl3): δ: 8.40 (br, 1H, CONHPh), 7.43 (d, 2H, J=7.7 Hz, 2Ha), 7.28 (d, 2H, J=7.7 Hz, Hb), 7.20 (m, 5H, 5xHd), 7.02 (t, 1H, J=7.4 Hz, Hc), 5.35 (d, 1H, J=7.8 Hz, CHNHBoc), 5.04 (d, 2H, J=2.6 Hz, BnOCH2), 4.26 (sa, 1H, CH2CHNHBOC), 2.60-2.52 (mc, 1H, 1xOCOCH2CH2), 2.46-2.38 (mc, 1H, 1x OCOCH2CH2), 2.21-2.12 (mc, 1H, 1xOCOCH2CH2), 1.99-1.90 (mc, 1H, 1x OCOCH2CH2), 1.40 (s, 9H, NHCO2C(CH3)3) ppm. MS: Positive mode [M + Na]+ = 435. MS: Negative mode [M + 2 H2O - H]- = 447. CAS nr: [126349-57-3]
94%		To a stirred solution of Boc-L-glutamic acid 5-benzyl ester [4a] (41 g, 122 mmol) in anhydrous CH2Cl2 (45 ml) at 0C, was added during 15 minutes a solution of DCC (30.1 g, 146 mmol) in anhydrous CH2Cl2 (45 ml). The resulting white solid was sonicated. After that, anhydrous aniline was added dropwise to the reaction mixture over 10 minutes at 0C (11.1 ml, 122 mmol). The mixture was stirred at room temperature for 40 minutes and filtered through Celite to remove insoluble material. The resulting liquid was evaporated to dryness and chromatographically purified, yielding the desired product (47.2 g, 94%). 1H-NMR (400 MHz, CDCl3): δ: 8.40 (br, 1H, CONHPh), 7.43 (d, 2H, J=7.7 Hz, 2Ha), 7.28 (d, 2H, J=7.7 Hz, Hb), 7.20 (m, 5H, 5xHd), 7.02 (t, 1H, J=7.4 Hz, Hc), 5.35 (d, 1H, J=7.8 Hz, CHNHBoc), 5.04 (d, 2H, J=2.6 Hz, BnOCH2), 4.26 (sa, 1H, CH2CHNHBoc), 2.60-2.52 (mc, 1H, 1xOCOCH2CH2), 2.46-2.38 (mc, 1H, 1x OCOCH2CH2), 2.21-2.12 (mc, 1H, 1xOCOCH2CH2), 1.99-1.90 (mc, 1H, 1x OCOCH2CH2), 1.40 (s, 9H, NHCO2C(CH3)3) ppm. MS: Positive mode [M + Na]+ = 435. MS: Negative mode [M + 2 H2O - H]- = 447. CAS nr: [126349-57-3]

94%		To a stirred solution of Boc-L-glutamic acid 5-benzyl ester [4a] (41 g, 122 mmol) in anhydrous CH2Cl2 (45 ml) at 0 C., was added during 15 minutes a solution of DCC (30.1 g, 146 mmol) in anhydrous CH2Cl2 (45 ml). The resulting white solid was sonicated. After that, anhydrous aniline was added dropwise to the reaction mixture over 10 minutes at 0 C. (11.1 ml, 122 mmol). The mixture was stirred at room temperature for 40 minutes and filtered through Celite to remove insoluble material. The resulting liquid was evaporated to dryness and chromatographically purified, yielding the desired product (47.2 g, 94%).1H-NMR (400 MHz, CDCl3): δ: 8.40 (br, 1H, CONHPh), 7.43 (d, 2H, J7.7 Hz, 2Ha), 7.28 (d, 2H, J=7.7 Hz, Hb), 7.20 (m, 5H, 5xHd), 7.02 (t, 1H, J=7.4 Hz, He), 5.35 (d, 1H, J=7.8 Hz, CHNHBoc), 5.04 (d, 2H, J=2.6 Hz, BnOCH2), 4.26 (sa, 1H, CH2CHNHBoc), 2.60-2.52 (mc, 1H, 1xOCOCH2CH2), 2.46-2.38 (mc, 1H, 1xOCOCH2CH2), 2.21-2.12 (mc, 1H, 1xOCOCH2CH2), 1.99-1.90 (mc, 1H, 1x OCOCH2CH2), 1.40 (s, 9H, NHCO2C(CH3)3) ppm.MS: Positive mode [M+Na]+=435.MS: Negative mode [M+2 H2O-H]-=447.CAS nr: [126349-57-3]
94%		Example 1; Preparation of intermediate [6a]: Benzyl 4-(tert-butoxycarbonyl-amino)-5-oxo-5-(phenylamino) pentanoate To a stirred solution of Boc-L-glutamic acid 5-benzyl ester [4a1 (41 g, 122 mmol) in anhydrous CH2Cl2 (45 ml) at 0 C., was added during 15 minutes a solution of DCC (30.1 g, 146 mmol) in anhydrous CH2Cl2 (45 ml). The resulting white solid was sonicated. After that, anhydrous aniline was added dropwise to the reaction mixture over 10 minutes at 0 C. (11.1 ml, 122 mmol). The mixture was stirred at room temperature for 40 minutes and filtered through Celite to remove insoluble material. The resulting liquid was evaporated to dryness and chromatographically purified, yielding the desired product (47.2 g, 94%).1H-NMR (400 MHz, CDCl3): δ: 8.40 (br, 1H, CONHPh), 7.43 (d, 2H, J=7.7 Hz, 2Ha), 7.28 (d, 2H, J=7.7 Hz, Hb), 7.20 (m, 5H, 5× Hd), 7.02 (t, 1H, J=7.4 Hz, HO, 5.35 (d, 1H, J=7.8 Hz, CHNHBoc), 5.04 (d, 2H, J=2.6 Hz, BnOCH2), 4.26 (sa, 1H, CH2CHNHBoc), 2.60-2.52 (mc, 1H, 1× OCOCH2CH2), 2.46-2.38 (mc, 1H, 1× OCOCH2CH2), 2.21-2.12 (mc, 1H, 1× OCOCH2CH2), 1.99-1.90 (mc, 1H, 1× OCOCH2CH2), 1.40 (s, 9H, NHCO2C(CH3)3) ppm.MS: Positive mode [M+Na]+=435.MS: Negative mode [M +2 H2O-H]-=447.CAS nr: [126349-57-3]
94%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 0.833333h;	To a stirred solution of Boc-L-glutamic acid 5-benzyl ester [4a] (41 g, 122 mmol) in anhydrous CH2Cl2 (45 ml) at 0 C., was added during 15 minutes a solution of DCC (30.1 g, 146 mmol) in anhydrous CH2Cl2 (45 ml). The resulting white solid was sonicated. After that, anhydrous aniline was added dropwise to the reaction mixture over 10 minutes at 0 C. (11.1 ml, 122 mmol). The mixture was stirred at room temperature for 40 minutes and filtered through Celite to remove insoluble material. The resulting liquid was evaporated to dryness and chromatographically purified, yielding the desired product (47.2 g, 94%).1H-NMR (400 MHz, CDCl3): δ: 8.40 (br, 1H, CONHPh), 7.43 (d, 2H, J=7.7 Hz, 2Ha), 7.28 (d, 2H, J=7.7 Hz, Hb), 7.20 (m, 5H, 5×Hd), 7.02 (t, 1H, J=7.4 Hz, Hc), 5.35 (d, 1H, J=7.8 Hz, CHNHBoc), 5.04 (d, 2H, J=2.6 Hz, BnOCH2), 4.26 (sa, 1H, CH2CHNHBoc), 2.60-2.52 (mc, 1H, 1×OCOCH2CH2), 2.46-2.38 (mc, 1H, 1×OCOCH2CH2), 2.21-2.12 (mc, 1H, 1×OCOCH2CH2), 1.99-1.90 (mc, 1H, 1×OCOCH2CH2), 1.40 (s, 9H, NHCO2C(CH3)3) ppm.MS: Positive mode [M+Na]+=435.MS: Negative mode [M+2H2O-H]-=447.CAS nr: [126349-57-3].

References: [1]Patent: WO2010/150205,2010,A1 .Location in patent: Page/Page column 23-24.
[2]Patent: EP2450349,2012,A1 .Location in patent: Page/Page column 16.
[3]Patent: EP2447249,2012,A1 .Location in patent: Page/Page column 16.
[4]Patent: US2012/129888,2012,A1 .Location in patent: Page/Page column 15.
[5]Patent: US2012/122950,2012,A1 .Location in patent: Page/Page column 11.
[6]Patent: US2012/142930,2012,A1 .Location in patent: Page/Page column 14.

27
[ 117997-81-6 ]
[ 75-65-0 ]
[ 1310037-42-3 ]

Yield	Reaction Conditions	Operation in experiment
69.5%	With dicyclohexyl-carbodiimide;dmap; In dichloromethane; at 20℃; for 1h;	1,1-Dioxo-[1,2]thiazinane-3-carboxylic acid tert-butyl ester; This compound was prepared with a modified method described in the Journal of Medicinal Chemistry 2004, 47, 2981-2983. 2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester (10 g, 29.6 mmol) was suspended in 80 ml of methylene chloride, 2-methyl-propan-2-ol (6.6 g, 88.9 mmol) was added and the reaction was cooled on ice-water bath. Dicyclohexylcarbodiimide (7.2 g, 34.4 mmol) was added slowly and followed by 4-dimethylaminopyridine (362 mg, 3.0 mmol). The reaction was stirred at room temperature for 1 hour. White solid was filtered and the filter cake was washed with methylene chloride. The filtrate was concentrated and the residue was treated with ether. After the solid was filtered off, the ether solution was washed with 0.5N HCl solution, brine and concentrated. The crude product was purified by using an ISCO (200 g) column chromatography, eluting with 5-20% ethyl acetate in hexanes to obtain 2-tert-butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-tert-butyl ester as a white solid. (8.1 g, 69.5%). LC-MS (ES) calculated for C21H31NO6, 393.5; found m/z 394.2 [M+H]+.

References: [1]Patent: US2011/136792,2011,A1 .Location in patent: Page/Page column 22.

28
[ 117997-81-6 ]
5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid [ No CAS ]