3-Amino-4-(1H-indol-3-yl)butanoic acid--hydrogen chloride (1/1) → (S)-N-(3,4,5-Trimethoxybenzyl)-N-methyl-2-[[(S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamino]N'-(t-butoxycarbonyl)-ethylamino]-3-phenyl-propionamide

HRID 235529Notes

Reaction equation

HRID 235529 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C@@H:9]([N:17]([CH2:25][CH:26]=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[NH:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]([CH2:47][C@H:48]([NH2:53])[CH2:49][C:50]([OH:52])=[O:51])=[CH:39]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C@@H:9]([N:17]([CH2:25][CH2:26][NH:53][C@H:48]([CH2:49][C:50]([OH:52])=[O:51])[CH2:47][C:40]1[C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[NH:38][CH:39]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 27615493-Amino-4-(1H-indol-3-yl)butanoic acid--hydrogen chloride (1/1)HCID 86750256(S)-N-(3,4,5-trimethoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Product 1

HCID 86750255(S)-N-(3,4,5-Trimethoxybenzyl)-N-methyl-2-[[(S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamino]N'-(t-butoxycarbonyl)-ethylamino]-3-phenyl-propionamide

Procedure

Prepare by the method of Example 1 using (S)-N-(3,4,5-trimethoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide (0.25 g, 1.0 mmol) and (S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamine hydrochloride salt ((S)-tryptophan methyl ester hydrochloride salt) (0.41 g, 1.0 mmol). Purify by chromatography eluting sequentially with 1% methanol/dichloromethane and 5% methanol/dichloromethane to give the title compound: TLC Rf =0.83 (silica gel, 10% methanol/dichloromethane).

Workup

  1. customPurify by chromatography
  2. washeluting sequentially with 1% methanol/dichloromethane and 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-2f780e2dfa3240c5aa204c2581a303cb
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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