Methanol → HCID 66738589, compound

HRID 557773Notes

Reaction equation

HRID 557773 reaction equation
C[O:2][C:3](=[O:42])[C@@H:4]([NH:8][C:9](=[O:41])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[N:26]=[C:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:28][C:29]=3[C:30]([F:33])([F:32])[F:31])=[O:24])=[CH:18][N:17]=2)=[C:12]([Cl:40])[CH:11]=1)[CH:5]([CH3:7])[CH3:6].CO.O.O.[OH-].[Li+]>O1CCCC1>[Cl:40][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[N:26]=[C:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[O:28][C:29]=2[C:30]([F:31])([F:33])[F:32])=[O:24])=[CH:18][N:17]=1)[C:9]([NH:8][CH:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:42])=[O:2])=[O:41]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57652106HCID 57652106, compound

Product 1

HCID 66738589HCID 66738589, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-(3-chloro-4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoylamino)-3-methyl-butyric acid methyl ester (30 mg, 0.05 mmol) in a mixture of tetrahydrofuran, methanol and water (3:1:1, 2 mL) was treated with lithium hydroxide monohydrate (6 mg, 0.15 mmol) at 50° C. for an hour. The reaction mixture was concentrated, diluted with water and the pH was adjusted to 1˜2 with dilute hydrochloric acid (1N). The white precipitate was collected by centrifugation, and then was dried under vacuum to give 2-(3-chloro-4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoylamino)-3-methyl-butyric acid (27 mg, 93%) as a white solid. LCMS calcd for C28H22ClF3N4O5 (m/e) 586, obsd 587 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. customThe white precipitate was collected by centrifugation
  4. customwas dried under vacuum

Sources & evidence

ORD record
ord-d72f0c7ce78941abb652e272ca03fa77
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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