Thioglycolic Acid → HCID 59434142, compound

HRID 508113Notes

Reaction equation

HRID 508113 reaction equation
[C:1]([NH:4][C:5]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([O:18][CH2:19][C:20]3([OH:28])[CH2:25][CH2:24][S:23](=[O:27])(=[O:26])[CH2:22][CH2:21]3)=[CH:13][C:12]=2[CH3:29])=[CH:9][C:8]([CH2:30][N:31](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:34]([F:45])[CH:33]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].SCC(O)=O.O.[OH-].[Li+]>CN(C)C=O.[Cl-].[Na+].O>[C:1]([NH:4][C:5]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([O:18][CH2:19][C:20]3([OH:28])[CH2:25][CH2:24][S:23](=[O:26])(=[O:27])[CH2:22][CH2:21]3)=[CH:13][C:12]=2[CH3:29])=[CH:9][C:8]([CH2:30][NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:34]([F:45])[CH:33]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 59434143HCID 59434143, compound

Product 1

HCID 59434142HCID 59434142, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 3-(4-{({6-(acetylamino)-4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate (246 mg, 0.30 mmol) and mercaptoacetic acid (62.6 μL, 0.90 mmol) in N,N-dimethylformamide (2 mL) was added lithium hydroxide monohydrate (75.5 mg, 1.80 mmol), and the mixture was stirred at room temperature for 3 days. Brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3-ethyl acetate) to give the title compound (176 mg, yield 92%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3-ethyl acetate)

Sources & evidence

ORD record
ord-07956bea4bd140f8bb03e3818bad4155
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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