5-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acid → 2,2-Dimethyl-propionic acid (R)-2-[(5-hydroxymethyl-7-nitro-1H-indole-2-carbonyl)-amino]-3-(4-methoxy-benzylsulfanyl)-propyl ester

HRID 336465Notes

Reaction equation

HRID 336465 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][C:7]([C:15]([OH:17])=O)=[CH:6]2.[NH2:18][C@@H:19]([CH2:28][S:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH2:20][O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][C:7]([C:15]([NH:18][C@@H:19]([CH2:28][S:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH2:20][O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:17])=[CH:6]2

Participants

3

Reactant 2

HCID 594480875-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acidHCID 595430572,2-Dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl ester

Product 1

HCID 595431102,2-Dimethyl-propionic acid (R)-2-[(5-hydroxymethyl-7-nitro-1H-indole-2-carbonyl)-amino]-3-(4-methoxy-benzylsulfanyl)-propyl ester

Procedure

5-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acid prepared in Preparation 38 and 2,2-dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl ester prepared in Preparation 31 were reacted according to the same procedure as Step B of Preparation 40 to give the title compound.

Workup

  1. customprepared in Preparation 31
  2. customwere reacted
  3. customaccording to the same procedure as Step B of Preparation 40

Sources & evidence

ORD record
ord-ca6c2be178db4972ac0d8ef78a6a27c9
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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