(1R,3S,5R)-3-(3-bromo-5-carboxy-phenylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester → 3-Bromo-5-{[(1R,3S,5R)-2-(1-carbamoyl-5-methoxy-1H-indol-3-ylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-3-carbonyl]-amino}-benzoic acid

HRID 1527548Notes

Reaction equation

HRID 1527548 reaction equation
C([O:5][C:6]([N:8]1[C@H:13]([C:14](=[O:26])[NH:15][C:16]2[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[C:18]([Br:25])[CH:17]=2)[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=O)(C)(C)C.[N:27]([C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[CH:37]=2)[N:32]([C:41]([NH2:43])=[O:42])[CH:31]=1)=C=O>O1CCOCC1>[Br:25][C:18]1[CH:19]=[C:20]([CH:21]=[C:16]([NH:15][C:14]([C@@H:13]2[CH2:12][C@@H:11]3[C@@H:9]([CH2:10]3)[N:8]2[C:6](=[O:5])[NH:27][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[CH:37]=3)[N:32]([C:41](=[O:42])[NH2:43])[CH:31]=2)=[O:26])[CH:17]=1)[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 68284370(1R,3S,5R)-3-(3-bromo-5-carboxy-phenylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl esterHCID 866738013-Isocyanato-5-methoxy-indole-1-carboxylic acid amide

Product 1

HCID 682834463-Bromo-5-{[(1R,3S,5R)-2-(1-carbamoyl-5-methoxy-1H-indol-3-ylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-3-carbonyl]-amino}-benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound (White solid) was prepared according to the general procedure described in Scheme D5 (Steps B and C) using (1R,3S,5R)-3-(3-bromo-5-carboxy-phenylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester) (prepared by using similar protocols as described in Scheme B7, except that the reaction mixture was heated at 65° C. in step A and dioxane was used instead of MeOH in step B) and 3-Isocyanato-5-methoxy-indole-1-carboxylic acid amide (prepared as described in Scheme A1). MS (LC/MS): 556.0 [M+H]+; tR (HPLC conditions c): 4.32 min.

Workup

  1. customprepared
  2. custom4.32 min.

Sources & evidence

ORD record
ord-0ec612edb9a34803a435052a517f4e84
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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