Dimethyl Sulfoxide → HCID 71075579, compound

HRID 2170651Notes

Reaction equation

HRID 2170651 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([C:25](=[O:38])[NH:26][C@H:27]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:37])[CH3:36])[CH:30]=4)[CH3:28])=[CH:22][CH:23]=3)[C:18]([CH3:39])=[C:17]2[CH3:40])=[CH:11][C:3]=1[O:4][C@@H:5]([CH3:10])[C:6]([O:8]C)=[O:7].CS(C)=O.O.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([C:25](=[O:38])[NH:26][C@H:27]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:36])[CH3:37])[CH:30]=4)[CH3:28])=[CH:22][CH:23]=3)[C:18]([CH3:39])=[C:17]2[CH3:40])=[CH:11][C:3]=1[O:4][C@@H:5]([CH3:10])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 14798Sodium HydroxideHCID 71075742HCID 71075742, compound

Product 1

HCID 71075579HCID 71075579, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The (S)-methyl 2-(2-chloro-5-((5-(((S)-1-(3-isopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenoxy)propanoate was dissolved in methanol (1.5 mL), DMSO (˜1.5 mL) and water (0.1 mL) then NaOH (2 N, 0.1 mL) was 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-da78d3c3ebb1491d8e96a022fafbdfa3
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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