Thioglycolic Acid → HCID 23157602, compound

HRID 508063Notes

Reaction equation

HRID 508063 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[C:26]([F:39])[CH:25]=3)[CH:17]=2)=[C:11]([CH3:52])[CH:10]=1)(=[O:5])=[O:4])[CH3:2].SCC(O)=O.O.[OH-].[Li+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])=[C:26]([F:39])[CH:25]=3)[CH:17]=2)=[C:11]([CH3:52])[CH:10]=1)(=[O:4])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 23157658HCID 23157658, compound

Product 1

HCID 23157602HCID 23157602, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 3-(4-{({4′-[2-(ethylsulfonyl)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate (1.67 g, 2.21 mmol) and mercaptoacetic acid (0.51 mL, 6.64 mmol) in N,N-dimethylformamide (17 mL) was added lithium hydroxide monohydrate (0.56 g, 13.3 mmol) under stirring at room temperature, and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate. and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/1) to give the title compound (1.17 g, yield 93%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hr
  2. washwashed with saturated aqueous sodium hydrogencarbonate
  3. dry with materialand saturated brine, dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-3863bbc4ee2243e9a6f5012d1c1d9131
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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