Thioglycolic Acid → HCID 59434133, compound

HRID 508109Notes

Reaction equation

HRID 508109 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:21][C:22]2[CH:23]=[C:24]([C:29]3[C:34]([CH3:35])=[CH:33][C:32]([O:36][CH2:37][C:38]4([OH:46])[CH2:43][CH2:42][S:41](=[O:45])(=[O:44])[CH2:40][CH2:39]4)=[CH:31][C:30]=3[CH3:47])[C:25]([CH3:28])=[CH:26][CH:27]=2)S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH:5]=[CH:4][C:3]=1[CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51].SCC(O)=O.O.[OH-].[Li+]>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:21][C:22]2[CH:23]=[C:24]([C:29]3[C:30]([CH3:47])=[CH:31][C:32]([O:36][CH2:37][C:38]4([OH:46])[CH2:39][CH2:40][S:41](=[O:44])(=[O:45])[CH2:42][CH2:43]4)=[CH:33][C:34]=3[CH3:35])[C:25]([CH3:28])=[CH:26][CH:27]=2)[CH:5]=[CH:4][C:3]=1[CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51]

Participants

6

Reactant 3

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 59434153HCID 59434153, compound

Product 1

HCID 59434133HCID 59434133, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 3-(2-fluoro-4-{({4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6,6′-trimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (189 mg, 0.24 mmol) and mercaptoacetic acid (50.1 μL, 0.72 mmol) in N,N-dimethylformamide (2 mL) was added lithium hydroxide monohydrate (60.4 mg, 1.44 mmol), and the mixture was stirred at room temperature for 2 days. Brine was added, 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=9/1-hexane/ethyl acetate=1/2) to give the title compound (133 mg, yield 93%) 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=9/1-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-5e6335c0520a41fea440471d2ab4300b
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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