Sodium Hydroxide → HCID 54765340, compound

HRID 2170629Notes

Reaction equation

HRID 2170629 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][C:25]3[CH:36]=[CH:35][C:28]([O:29][CH2:30][C:31]([O:33]C)=[O:32])=[CH:27][CH:26]=3)[C:19]([CH3:37])=[C:18]4[CH3:38])=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][C:25]3[CH:36]=[CH:35][C:28]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:26]=3)[C:19]([CH3:37])=[C:18]4[CH3:38])=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71075406HCID 71075406, compound

Product 1

HCID 54765340HCID 54765340, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the (S)-methyl 2-(4-((5-((1-(3-cyclopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenoxy)acetate in methanol (1 mL) was added a 5N NaOH solution (1 mL). The resulting solution was heated at 50° C. for 4 h, and then quenched carefully by addition of a 6N HCl solution (1 mL). The mixture was diluted with ethyl acetate, washed with a 0.5 N HCl solution and brine, dried on MgSO4, and concentrated. The resulting oil was purified by preparative HPLC to afford a white powder (46 mg). ESI-MS (m/z): 497 [MH]+

Workup

  1. customquenched carefully by addition of a 6N HCl solution (1 mL)
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with a 0.5 N HCl solution and brine
  4. customdried on MgSO4
  5. concentrationconcentrated
  6. customThe resulting oil was purified by preparative HPLC

Sources & evidence

ORD record
ord-878df36421884bb3a3528a35eed8f68f
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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