Water → HCID 71075558, compound

HRID 2170660Notes

Reaction equation

HRID 2170660 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@@H:7]([CH3:12])[C:8]([O:10]C)=[O:9])=[CH:4][C:3]=1[CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](=[O:38])[NH:26][C@H:27]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:37])[CH3:36])[CH:30]=3)[CH3:28])=[CH:22][CH:23]=2)[C:18]([CH3:39])=[C:17]1[CH3:40].O.[OH-].[Na+]>CO.CS(C)=O>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@@H:7]([CH3:12])[C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](=[O:38])[NH:26][C@H:27]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:36])[CH3:37])[CH:30]=3)[CH3:28])=[CH:22][CH:23]=2)[C:18]([CH3:39])=[C:17]1[CH3:40]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 71075200HCID 71075200, compound

Product 1

HCID 71075558HCID 71075558, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

The (S)-methyl 2-(4-chloro-3-((5-(((S)-1-(3-isopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenoxy)propanoate was dissolved in methanol (1.5 mL) and DMSO (˜1 mL), water (0.1 mL) and NaOH (2 N, 0.1 mL) were added dropwise. The reaction was monitored by LC/MS. It was stirred until all the starting material was consumed (˜3 h). It was acidified with trifluoroacetic acid, filtered and purified by preparative HPLC to yield the title compound. ESI-MS (m/z): 547.1 [M+H]+.

Workup

  1. customwas consumed (˜3 h)
  2. filtrationfiltered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2b0dc0b6b7634ae292dbdbd16870e2c3
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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