3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester

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Chemical Name:3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester
CAS No.:354117-31-0
Molecular Formula:C₃₇H₃₇N₃O₅
Molecular Weight:603.718
Hs Code.:

Synonyms:3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester

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Chemical Property of 3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester

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Technology Process of 3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester

There total 8 articles about 3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 2627-86-3
(S)-1-phenyl-ethylamine

: 354117-28-5
3-((R)-2-benzyloxycarbonylamino-2-carboxy-butyl)-indole-1-carboxylic acid benzyl ester

: 354117-31-0
3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester

Guidance literature:: 3-((R)-2-benzyloxycarbonylamino-2-carboxy-butyl)-indole-1-carboxylic acid benzyl ester; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

(S)-1-phenyl-ethylamine; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 8h; Further stages.;
DOI:10.1021/jm010825z

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 354117-31-0
3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / aq. Na₂CO₃ / dioxane / 16 h / 20 °C

2.1: LHMDS; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 2 h / -78 °C

2.2: 79 percent / tetrahydrofuran / -78 - 20 °C

3.1: 69 percent / TFA / CH₂Cl₂ / 24 h / 20 °C

4.1: 95 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 20 °C

5.1: HBTU; DIPEA / dimethylformamide / 0.17 h / 20 °C

5.2: 80 percent / DIPEA / dimethylformamide / 8 h

With morpholine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm010825z

Reference yield:

: 354117-18-3
(2R,3aS,8aS)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 2-allyl ester 1-benzyl ester

: 354117-31-0
3-[(R)-2-benzyloxycarbonylamino-2-((S)-1-phenyl-ethylcarbamoyl)-butyl]-indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / aq. Na₂CO₃ / dioxane / 16 h / 20 °C

2.1: LHMDS; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 2 h / -78 °C

2.2: 79 percent / tetrahydrofuran / -78 - 20 °C

3.1: 69 percent / TFA / CH₂Cl₂ / 24 h / 20 °C

4.1: 95 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 20 °C

5.1: HBTU; DIPEA / dimethylformamide / 0.17 h / 20 °C

5.2: 80 percent / DIPEA / dimethylformamide / 8 h

With morpholine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm010825z