5-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acid → (R)-2-[(5-chloromethyl-7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid methylester

HRID 336466Notes

Reaction equation

HRID 336466 reaction equation
O[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](O)=O)=[CH:6]2.[ClH:18].[CH3:19][O:20][C:21](=[O:36])[CH2:22][C@@H:23]([NH2:35])[CH2:24][S:25]CC1C=CC(OC)=CC=1>>[CH3:19][O:20][C:21](=[O:36])[CH2:22][C@@H:23]1[CH2:24][S:25][C:15]([C:7]2[NH:8][C:9]3[C:5]([CH:6]=2)=[CH:4][C:3]([CH2:2][Cl:18])=[CH:11][C:10]=3[N+:12]([O-:14])=[O:13])=[N:35]1

Participants

3

Reactant 2

HCID 594480875-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acidHCID 66974362(R)-3-amino-4-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester hydrochloride

Product 1

HCID 59543007(R)-2-[(5-chloromethyl-7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid methylester

Procedure

5-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acid prepared in Preparation and (R)-3-amino-4-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester hydrochloride prepared in Preparation 27 were reacted according to the same procedures as Steps B and C of Preparation 40 to give the title compound.

Workup

  1. customprepared in Preparation 27
  2. customwere reacted
  3. customaccording to the same procedures as Steps B and C of Preparation 40

Sources & evidence

ORD record
ord-3c53b81eed6c49e68de10e8f81c0ceb0
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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