125238-99-5|Fmoc-Dab(Boc)-OH| Ambeed

CAS No. :	125238-99-5
Formula :	C₂₄H₂₈N₂O₆
M.W :	440.49
SMILES Code :	O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CCNC(OC(C)(C)C)=O
MDL No. :	MFCD00151941
InChI Key :	LIWKOFAHRLBNMG-FQEVSTJZSA-N
Pubchem ID :	2756101

Safety of [ 125238-99-5 ]

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

Application In Synthesis of [ 125238-99-5 ]

* 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 [ 125238-99-5 ]

[ 125238-99-5 ] Synthesis Path-Downstream 1~54

1
[ 20866-48-2 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 125238-99-5 ]
[ 110116-75-1 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2094 - 2099.

2
[ 811434-05-6 ]
[ 35661-60-0 ]
[ 125238-99-5 ]
[ 117872-75-0 ]
Fmoc-D-Phe-OH [ No CAS ]
C₈₁H₉₂Cl₃N₁₁O₁₇ [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 1915 - 1924.

3
[ 811434-05-6 ]
[ 35661-60-0 ]
[ 125238-99-5 ]
[ 117872-75-0 ]
Fmoc-D-Phe-OH [ No CAS ]
C₉₃H₁₀₅Cl₄N₁₃O₂₀ [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 1915 - 1924.

4
[ 811434-05-6 ]
[ 35661-60-0 ]
[ 125238-99-5 ]
[ 117872-75-0 ]
Fmoc-D-Phe-OH [ No CAS ]
C₁₀₄H₁₁₈Cl₄N₁₄O₂₂ [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 1915 - 1924.

5
[ 811434-05-6 ]
[ 35661-60-0 ]
[ 125238-99-5 ]
[ 117872-75-0 ]
Fmoc-D-Phe-OH [ No CAS ]
Fmoc-L-α,γ-diaminobutyryl(2-ClZ)-Thr(Bzl)-L-α,γ-diaminobutyryl(2-ClZ)-L-α,γ-diaminobutyryl-L-α,γ-diaminobutyryl(2-ClZ)-d-Phe-Leu-L-α,γ-diaminobutyryl(2-ClZ)-L-α,γ-diaminobutyryl(2-ClZ)-Thr(Bzl)-OH [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 1915 - 1924.

6
(S)-(3-fluoren-9-yl-9-methoxycarbonyl)-4-[2-(tert-butyloxycarbonylamino)ethyl]-5-oxazolidinone [ No CAS ]
[ 125238-99-5 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 2901 - 2912.

7
[ 14464-29-0 ]
[ 125238-99-5 ]
Fmoc-L-Arg^NO₂ [ No CAS ]
[ 76-05-1 ]
N^α-acetyl-L-Arg^NO2-LDbu-NH2 [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2938 - 2945.

8
[ 71989-35-0 ]
[ 135112-28-6 ]
[ 125238-99-5 ]
3-allyloxycarbonylamino-benzoic acid [ No CAS ]
benzoic anhydride [ No CAS ]
p-nitrobenzylamine [ No CAS ]
Bz-Dab-Nva-Thr-(3-aminobenzoyl)-NHCH₂PhNO₂ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 93 - 99.

9
C₂₇H₂₂N₂O₉S [ No CAS ]
[ 125238-99-5 ]
[ 116821-47-7 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
C₇₇H₁₂₂N₃₄O₁₇S [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 1515 - 1520.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5129 - 5132.

10
[ 918428-66-7 ]
[ 125238-99-5 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 2901 - 2912.

11
[ 159530-17-3 ]
[ 125238-99-5 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 2901 - 2912.

12
[ 71989-20-3 ]
Fmoc-Ala [ No CAS ]
[ 125238-99-5 ]

References: [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 1915 - 1924.

13
[ 125238-99-5 ]
4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester; hydrochloride [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 1041 - 1043.

14
[ 125238-99-5 ]
[ 668985-71-5 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 1041 - 1043.

15
[ 125238-99-5 ]
[ 688316-86-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2199 - 2203.

16
[ 125238-99-5 ]
[ 456527-46-1 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1021 - 1024.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2514 - 2529.
[3]Patent: WO2006/123020,2006,A1 .

17
[ 125238-99-5 ]
[ 315203-40-8 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1021 - 1024.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2514 - 2529.

18
[ 125238-99-5 ]
tert-butyl ((S)-3-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(3,4-difluorophenyl)propanamido)-4-(benzylamino)-4-oxobutyl)carbamate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1021 - 1024.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2514 - 2529.

19
[ 125238-99-5 ]
{3-benzylcarbamoyl-3-[2-{3-[1-(2,6-dichloro-benzyl)-3-pyrrolidin-1-ylmethyl-1H-indazol-6-yl]-ureido}-3-(3,4-difluoro-phenyl)-propionylamino]-propyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1021 - 1024.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2514 - 2529.

20
[ 125238-99-5 ]
[ 125279-44-9 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2938 - 2945.

21
[ 125238-99-5 ]
[ 291529-79-8 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2938 - 2945.

22
[ 118-31-0 ]
[ 125238-99-5 ]
[ 369656-01-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With benzotriazol-1-ol; diisopropyl-carbodiimide; In DMF (N,N-dimethyl-formamide); dichloromethane; at 50℃;	Fmoc-Dbu (Boc) -OH (100 mg, 440.5 G/MOL, 0.23 mmol, 1 eq), DIC (36 mul, 126.20 G/MOL, 0.806 G/CM3, 0.23 mmol, 1 eq) and HOBt (31 mg, 135.12 G/MOL, 0.23 MMOL, 1 eq) were dissolved in dry DMF/DCM (1/1,3 ML). After 5 minutes 1-NAPHTHYLMETHYLAMINE (33 1LL, 157.22 g/mol, 1.092 G/CM3, 0.23 MMOL, 1 eq, Fluka) was added to the reaction mixture. After overnight stirring at 50°C, solvent was evaporated and the residue was dissolved in 30 ML ETHYL acetate and washed three times with 20 ml water. Organic phase was dried with NA2SO4 and evaporated. Residue was purified with flash chromatography. 78.5 mg of 4-N-BOC-AMINO- (S)-2-N -FMOC-AMINO-N"-1-NAPHTHYLMETHYLBUTAN- amide was obtained, yield 60percent.

References: [1]Patent: WO2005/33069,2005,A1 .Location in patent: Page/Page column 28.

23
[ 125238-99-5 ]
[ 13078-79-0 ]
[ 849948-71-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-ol; diisopropyl-carbodiimide; In DMF (N,N-dimethyl-formamide); dichloromethane; at 35℃;	Fmoc-Dbu (Boc) -OH (250.8 mg, 440.5 G/MOL, 0.57 MMOL, 1 eq), DIC (89 mul, 126.20 g/mol, 0. 806 G/CM3, 0.57 mmol, 1 eq) and HOBt (77.6 mg, 135.12 g/mol, 0.57 mmol, 1 eq) were dissolved in dry DMF/DCM (1/1,6 ml). After 5 minutes 2- (3-CHLOROPHENYL) ETHYLAMINE (79 ; J, 155.63 g/mol, 1.119 G/CM3, 0.57 mmol, 1 eq) was added to the reaction mixture. Temperature was raised to 35°C and mixture stirred overnight. Solvent was then evaporated and residue dissolved in DCM, which was washed twice with water and once with brine. Organic phase was subsequently dried with NA2SO4 and evaporated. Residue was purified with silica column chromatography (mobile phase starting from DCM up to 5percent MEOH in DCM). 4- (N-Boc-amino)-N'-2- (3-chloro- phenyl) ethyl- (S)-2- (N"-Fmoc-amino) butanamide was obtained with quantita- tive yield.

References: [1]Patent: WO2005/33069,2005,A1 .Location in patent: Page/Page column 29.

24
[ 541-41-3 ]
[ 125238-99-5 ]
C₂₇H₃₂N₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at -5℃; for 0.5h;	Example 3; Synthesis of (S)-4-methyInaphthalene-1 -sulfonic acid (3-amino-1-benzyl- oxymethylpropyl)amide (compound 3); Step .; [0073] Fmoc-/--Dab(Boc)-OH (402 mg, 440.50 g/mol 0,91 mmol, 1 eq) was dissolved in dry THF (10 ml). TEA (132 mul, 0,95 mrno., 1 eq) was added and the resulting mixture was cooled to -5 0C in an ice/salt bath. Ethyl chloro- formate (91 mul, 108.53 g/mol, 1.135 g/cm3, 0.95 mmol, 1 eq) was added drop- wise to the mixture. After a 30 min reaction time the formed precipitate was filtered off. The filtrate was added dropwise to a freshly prepared and cooled (-50C) solution of sodium borohydride (43.7mg, 37.83 g/mol, 1.16 mmol, 1.3 eq) in 2 ml of H2O/THF. The resulting mixture was stirred at -5 0C for 1.5 h and then allowed to warm up to room temperature. The solvent was evaporated and the residue dissolved in EtOAc (30 ml) before it was washed successively with a 10percent citric acid solution, a 5percent NaHCO3 solution, water and brine. The organic phase was dried over Na2SO4. Filtration and evaporation gave a crude product which was purified by chromatography to obtain 282 mg (72 percent yield) of (S)-4-(Lambda/-Boc- amino)-2-(A/'-Fmoc-amino)butan-1-ol.

References: [1]Patent: WO2006/123020,2006,A1 .Location in patent: Page/Page column 33.

25
[ 61-54-1 ]
[ 79-11-8 ]
[ 125238-99-5 ]
[ 1000787-30-3 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 6133 - 6143.

26
C₁₅H₁₉N₄O₄Pol [ No CAS ]
[ 125238-99-5 ]
C₃₉H₄₅N₆O₉Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		0.65 g of resin 5a are divided into 5 aliquots. 0.65 g of resin 5b are divided into two equal portions. 0.45 mmol of each N-protected amino acids 6a-f (6a: N(alpha)-Fmoc-N(gamma)-Boc-L-2,4-diaminobutyric acid, twice; 6b: Fmoc-(OTrt)-L-homoserine; 6c: Fmoc-Asp(OtBu)-OH; 6d: Fmoc-Trp(Boc)-OH; 6e: Fmoc-L-4-MePhe-OH; 6f: Fmoc-L-(4-Boc-aminomethyl)Phe-OH each are dissolved in solutions of 5 mL of DMF, 93 muL of DIC and 92 mg of HOBt*H2O. The solutions obtained are stirred for 30 minutes at rt. The solution of activated 6a obtained is divided into 2 equal portions. The portions are transferred to an aliquot of resin 5a and resin 5b to give the side chain protected resins 7a and 8a, respectively. The solutions of activated 6b-e obtained are transferred to the remaining aliquots of resin 5a to give protected resins 7b-e. The solution containing 6f is transferred to the second aliquot of resin 5b to give protected resin 8b. After shaking for 16.5 hours at rt the resins obtained are filtered off and washed with DMF (9.x.10 mL), DCM (6.x.10 mL) and MeOH (6.x.10 mL). The fully protected resins 7a-e and 8a-b obtained are dried under reduced pressure. All chloranil tests are negative.

References: [1]Patent: US2009/5419,2009,A1 .Location in patent: Page/Page column 9-10.

27
[ 120-43-4 ]
[ 125238-99-5 ]
[ 1163792-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethylmorpholine;; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 0℃; for 1h;	Example 92: 4-[(S)-4-Acetylamino-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1- yl)-2-oxo-ethoxy]-1 -phenyl-1 H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1 - carboxylic acid ethyl ester; i) 4-[(S)-4-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)- butyryl]-piperazine-1 -carboxylic acid ethyl ester; To a solution of 1.33 ml 1-ethoxycarbonylpiperazine, 1.27 ml N-ethylmorpholine and 4.0 g N-alpha-Fmoc-N-beta-Boc-L-diaminobutyric acid in 40 ml DMF were added 2.98 g TOTU at 0 0C. After 1 h the reaction mixture was diluted with 100 ml ethyl acetate and subsequently extracted with aqueous LiCI (4 percent), half-saturated aqueous NaHCO3 and water. The crude <n="118"/>product obtained after evaporation of the solvent was used in the subsequent reaction. Yield: 4.96 g colorless foam.

References: [1]Patent: WO2009/80226,2009,A2 .Location in patent: Page/Page column 116-117.

28
C₂₆H₂₈N₂O₃ [ No CAS ]
[ 125238-99-5 ]
[ 1185653-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;	Example 28 Synthesis of Compound 28 (S)-9-fluorenylmethyl 10-(2,2-diphenylethyl)-2,2-dimethyl-18-phenyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaoctadecan-8-ylcarbamate To 2,2-diphenylethylamine (0.95 g, 7.4 mmol) in DCM (10 mL) was added the alpha,beta-unsaturated ketone 27 (5.7 mmol) in DCM (75 mL). After stirring at room temperature for 15 mins, Fmoc-L-2,4-diaminobutyric acid(Boc)-OH (2.4 g, 8.55 mmol) and DIC (0.87 mL, 5.6 mmol) were added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum ether:EtOAc (1:1 to 0:1) to give 28 (1.5 g, 31percent) Alternatively, to 2,2-diphenylethylamine (0.97 g, 7.4 mmol) in DCM (20 mL) was added the alpha,beta-unsaturated ketone 27 (5.95 mmol) in DCM (40mL). After stirring at room temperature for 15 mins, Fmoc-L-2,4-diaminobutyric acid(Boc)-OH (2.4 g, 8.55 mmol), DIPEA (2.5 mL) and HATU (2.3 g, 6.0 mmol) were added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was taken up in EtOAc (100 mL). The organic layer was washed with saturated sodium bicarbonate solution (2100 mL), saturated ammonium chloride solution (2100 mL) and brine (2*100 mL). The organic phase was dried and the solvent removed under reduced pressure. The residue was subjected to column chromatography on silica gel using petroleum ether:EtOAc (3:1 to 1:1 to 0:1) to give 28 (0.86 g, 17percent).
	With diisopropyl-carbodiimide; In dichloromethane; at 20℃;	Example 28 Synthesis of Compound 28 (S)-9-fluorenylmethyl 10-(2,2-diphenylethyl)-2,2-dimethyl-18-phenyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaoctadecan-8-ylcarbamate To 2,2-diphenylethylamine (0.95 g, 7.4 mmol) in DCM (10 mL) was added the alpha,beta-unsaturated ketone 27 (5.7 mmol) in DCM (75 mL). After stirring at room temperature for 15 mins, Fmoc-L-2,4-diaminobutyric acid(Boc)-OH (2.4 g, 8.55 mmol) and DIC (0.87 mL, 5.6 mmol) were added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum ether:EtOAc (1:1 to 0:1) to give 28 (1.5 g, 31percent)

References: [1]Patent: US2009/221557,2009,A1 .Location in patent: Page/Page column 119.
[2]Patent: US2009/221557,2009,A1 .Location in patent: Page/Page column 119.

29
C₂₂H₂₈N₂O₃ [ No CAS ]
[ 125238-99-5 ]
[ 1185653-65-9 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl-carbodiimide; In dichloromethane; at 20℃;	Example 34 Synthesis of Compound 34 (S)-9-fluorenylmethyl 10-(2-phenylbutyl)-2,2-dimethyl-18-phenyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaoctadecan-8ylcarbamate To 2-phenylbutylamine hydrochloride (0.26 g, 1.4 mmol) in DCM (10 mL) and DIPEA (0.25 mL, 1.8 mmol) was added the alpha,beta-unsaturated ketone 27 (1.06 mmol) in DCM (20 mL). After stirring at room temperature for 15 mins, Fmoc-diaminobutyric acid(Boc)-OH (0.7 g, 1.56 mmol) and DIC (0.25 mL, 1.61 mmol) were added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum ether:EtOAc (1:1 to 0:1), providing Compound 34 as a mixture of diastereomers (0.17 g, 21percent).

References: [1]Patent: US2009/221557,2009,A1 .Location in patent: Page/Page column 121.

30
C₁₅H₁₈Cl₂N₂O₃ [ No CAS ]
[ 125238-99-5 ]
[ 1185653-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl-carbodiimide; In dichloromethane; at 20℃;	Example 45 Synthesis of Compound 46 (S)-9-fluorenylmethyl 10-(3,5-dichlorobenzyl)-2,2-dimethyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaiscos-19-en-8-ylcarbamate To 3,5-dichlorobenzylamine (0.49 g, 2.8 mmol) in DCM (5 mL) was added the alpha,beta-unsaturated ketone 45 (2.12 mmol) in DCM (10 mL). After stirring at room temperature for 15 mins, Fmoc-diaminobutyric acid(Boc)-OH (1.35 g, 3.1 mmol) and DIC (0.5 mL, 3.2 mmol) was added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum ether:EtOAc (1:1 to 0:1), providing compound 46 (0.48 g, 22percent).

References: [1]Patent: US2009/221557,2009,A1 .Location in patent: Page/Page column 124.

31
C₂₇H₂₂N₂O₉S [ No CAS ]
[ 125238-99-5 ]
[ 116821-47-7 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
C₂₃H₁₈N₂O₆S [ No CAS ]
C₅₄H₁₀₄N₃₂O₁₁ [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 1515 - 1520.

32
[ 35661-40-6 ]
[ 71989-18-9 ]
[ 125238-99-5 ]
[ 135673-97-1 ]
N-[(9-fluorenyl)methoxycarbonyl]-4-chloro-L-phenylalanine [ No CAS ]
[ 1186310-44-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5229 - 5237.

33
[ 71989-18-9 ]
[ 132684-59-4 ]
[ 77284-32-3 ]
[ 135112-28-6 ]
[ 125238-99-5 ]
N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine [ No CAS ]
[ 1349220-85-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5229 - 5237.

34
[ 132684-59-4 ]
[ 125238-99-5 ]
[ 135673-97-1 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 1186310-46-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5229 - 5237.

35
[ 811434-05-6 ]
Fmoc-Ala-O-Wang resin [ No CAS ]
[ 124-07-2 ]
[ 35661-60-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 117872-75-0 ]
C₁₀₁H₁₂₇Cl₅N₁₆O₂₃ [ No CAS ]