Hydrochloric Acid → HCID 16035473, compound

HRID 1783409Notes

Reaction equation

HRID 1783409 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C@@H:14]2[CH2:20][C:19]([F:22])([F:21])[CH2:18][CH2:17][NH:16][C:15]2=[O:23])=[CH:8][CH:7]=1.[Li+].[OH-].O.Cl>CO.C(OCC)(=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([N:13]([CH2:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:11][CH:10]=2)[C@@H:14]2[CH2:20][C:19]([F:22])([F:21])[CH2:18][CH2:17][NH:16][C:15]2=[O:23])(=[O:26])=[O:25])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68623745HCID 68623745, compound

Product 1

HCID 16035473HCID 16035473, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-{[(4-chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-propionic acid methyl ester (65 mg, 0.13 mmol) was dissolved in methanol (0.5 ml) and treated with 2 N LiOH in water (0.25 ml, 0.5 mmol) overnight at 40° C. The reaction mixture was distributed between 4 N HCl and ethyl acetate. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude product (50 mg) was purified using column chromatography (dichloromethane/methanol 90:10) to yield 45 mg (71%);

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product (50 mg) was purified
  4. customto yield 45 mg (71%)

Sources & evidence

ORD record
ord-0f2e800efc1d45beb78286d4b4663b8b
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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