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

HRID 235528Notes

Reaction equation

HRID 235528 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[CH2:5][N:6]([CH3:28])[C:7](=[O:27])[C@@H:8]([N:16]([CH2:24][CH:25]=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([CH2:43][C@H:44]([NH2:49])[CH2:45][C:46]([OH:48])=[O:47])=[CH:35]1>>[CH3:1][O:2][C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[CH2:5][N:6]([CH3:28])[C:7](=[O:27])[C@@H:8]([N:16]([CH2:24][CH2:25][NH:49][C@H:44]([CH2:45][C:46]([OH:48])=[O:47])[CH2:43][C:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[NH:34][CH:35]=1)[C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 27615493-Amino-4-(1H-indol-3-yl)butanoic acid--hydrogen chloride (1/1)HCID 86750254(S)-N-(2-methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Product 1

HCID 86750253(S)-N-(2-Methoxybenzyl)-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-(2-methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide (0.71 g, 1.6 mmol) and (S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamine hydrochloride salt ((S)-tryptophan methyl ester hydrochloride salt) (0.45 g, 1.76 mmol). Purify by chromatography eluting with 50% ethyl acetate/hexane to give the title compound: TLC Rf =0.56 (silica gel, 50% ethyl acetate/hexane)

Workup

  1. customPurify by chromatography
  2. washeluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-fbd2011306d34402ae411206f0e5ca49
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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