Thioglycolic Acid → Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoate

HRID 508091Notes

Reaction equation

HRID 508091 reaction equation
[C:1]1([CH:7]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[O:8][C:9]2[CH:42]=[CH:41][C:12]([CH2:13][N:14](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([F:28])[CH:16]=3)=[CH:11][C:10]=2[CH2:43][CH:44]([CH3:46])[CH3:45])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.SCC(O)=O.O.[OH-].[Li+].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]1([CH:7]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[O:8][C:9]2[CH:42]=[CH:41][C:12]([CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([F:28])[CH:16]=3)=[CH:11][C:10]=2[CH2:43][CH:44]([CH3:46])[CH3:45])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 23157541Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

Product 1

HCID 23157631Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoateYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate (0.80 g, 1.10 mmol) and mercaptoacetic acid (0.17 mL, 2.45 mmol) in N,N-dimethylformamide (15 mL) was added lithium hydroxide monohydrate (0.20 g, 4.77 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was poured into 10% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane=3/97-15/85) to give the title compound (552 mg, yield 93%) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9ed7781179a4f35ba8123f196f25567
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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