Water → HCID 73507392, compound

HRID 594828Notes

Reaction equation

HRID 594828 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][C@H:14]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH:33]3[CH2:35][CH2:34]3)(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:15]([NH:17][C:18]2[S:19][C:20]([F:23])=[CH:21][N:22]=2)=[O:16])[CH2:9]1)=[O:7])(=O)C.[OH-].[Na+].O>O1CCCC1.CO>[CH:33]1([S:30]([C:27]2[CH:26]=[CH:25][C:24]([C@@H:14]([CH2:13][C@H:10]3[CH2:11][CH2:12][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:9]3)[C:15]([NH:17][C:18]3[S:19][C:20]([F:23])=[CH:21][N:22]=3)=[O:16])=[CH:29][CH:28]=2)(=[O:31])=[O:32])[CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 118268316HCID 118268316, compound

Product 1

HCID 73507392HCID 73507392, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-((S)-3-((R)-2-(4-(Cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidin-1-yl)-2-oxoethyl acetate (47.0 mg, 89.8 μmol) was dissolved in tetrahydrofuran (1 mL) and methanol (1 mL), and thereafter, an aqueous solution of sodium hydroxide (2 M, 0.36 mL) was added to the obtained solution under ice-cold condition. The obtained mixture was stirred for 30 minutes. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated in vacuo. The obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→15%) to obtain the captioned compound (38.2 mg, 88%) in the form of a white solid.

Workup

  1. extractionthe mixed solution was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated in vacuo
  4. customThe obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→15%)

Sources & evidence

ORD record
ord-bede8e1820544e0e952bec39fda1183d
Source dataset
uspto-grants-2016_01
Patent number
US09242978B2

Reaction notes

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