(R)-3-amino-4-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester hydrochloride → (R)-2-[5-methanesulfonylmethyl-7-nitro-1H-indol-2-yl]-4,5-dihydro-thiazol-4-yl-acetic acid methyl ester

HRID 1515259Notes

Reaction equation

HRID 1515259 reaction equation
CO[C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:9][C:8]=2[N+:19]([O-:21])=[O:20])=O.Cl.[CH3:23][O:24][C:25](=[O:40])[CH2:26][C@@H:27]([NH2:39])[CH2:28][S:29]CC1C=CC(OC)=CC=1>>[CH3:23][O:24][C:25](=[O:40])[CH2:26][C@@H:27]1[CH2:28][S:29][C:3]([C:5]2[NH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([CH2:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:9][C:8]=3[N+:19]([O-:21])=[O:20])=[N:39]1

Participants

3

Reactant 2

HCID 66974362(R)-3-amino-4-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester hydrochlorideHCID 68485619(5-Methanesulfonylmethyl-7-nitro-1H-indol-2-yl)-carboxylic acid methylester

Product 1

HCID 59543053(R)-2-[5-methanesulfonylmethyl-7-nitro-1H-indol-2-yl]-4,5-dihydro-thiazol-4-yl-acetic acid methyl ester

Procedure

(5-Methanesulfonylmethyl-7-nitro-1H-indol-2-yl)-carboxylic acid methylester prepared in Step A of Preparation 44 and (R)-3-amino-4-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester hydrochloride prepared in Preparation 27 were reacted according to the same procedure as Preparation 40 to give the title compound.

Workup

  1. customprepared in Preparation 27
  2. customwere reacted
  3. customaccording to the same procedure as Preparation 40

Sources & evidence

ORD record
ord-2bd30eae16d54502a1372543fcdc260a
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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