(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid → 1-(n-Benzyloxycarbonyl-2(s)-aminobutyryl)-2(s)-indolinecarboxylic acid n-butylamide

HRID 2185667Notes

Reaction equation

HRID 2185667 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([NH:22][C:23]([C@@H:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26]1)=[O:24])[CH2:19][CH2:20][CH3:21]>>[CH2:18]([NH:22][C:23]([C@@H:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]1[C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:16][CH3:17])=[O:24])[CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acidHCID 114133182(s)-Indolinecarboxylic acid n-butylamide

Product 1

HCID 115249331-(n-Benzyloxycarbonyl-2(s)-aminobutyryl)-2(s)-indolinecarboxylic acid n-butylamide

Procedure

The process is performed as in Example 15 c), using 0.646 g (2.73 mmol) of N-benzyloxycarbonyl-2(S)-aminobutyric acid prepared as in Example 3 a) and 0.595 g (2.73 mmol) of the amide prepared in step b). An oil is obtained which is recrystallized from CCl4.

Workup

  1. customAn oil is obtained which
  2. customis recrystallized from CCl4

Sources & evidence

ORD record
ord-542825ccd3e84971a76bb75cebfd81be
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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