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

HRID 235530Notes

Reaction equation

HRID 235530 reaction equation
[CH2:1]([N:8]([CH3:31])[C:9](=[O:30])[C@@H:10]([N:18]([CH2:26][CH2:27][CH:28]=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]([CH2:42][C@H:43]([NH2:48])[CH2:44][C:45]([OH:47])=[O:46])=[CH:34]1>>[CH2:1]([N:8]([CH3:31])[C:9](=[O:30])[C@@H:10]([N:18]([CH2:26][CH2:27][CH2:28][NH:48][C@H:43]([CH2:44][C:45]([OH:47])=[O:46])[CH2:42][C:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH:33][CH:34]=1)[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27615493-Amino-4-(1H-indol-3-yl)butanoic acid--hydrogen chloride (1/1)HCID 86750258(S)-N-benzyl-N-methyl-2-[N'-(t-butoxycarbonyl)-3-oxo-propylamino]-3-phenyl-propionamide

Product 1

HCID 86750257(S)-N-Benzyl-N-methyl-2-[[(S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamino]-N'-(t-butoxycarbonyl)-propylamino]-3-phenyl-propionamide

Procedure

Prepare by the method of Example 1 using (S)-N-benzyl-N-methyl-2-[N'-(t-butoxycarbonyl)-3-oxo-propylamino]-3-phenyl-propionamide (2 mmol) and (S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamine hydrochloride salt ((S)-tryptophan methyl ester hydrochloride salt) (2 mmol). Purify by chromatography to give the title compound.

Workup

  1. customPurify by chromatography

Sources & evidence

ORD record
ord-5e23e12cf4a74bd79d1352bf3cced2ae
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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