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

HRID 508091
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HRID 508091 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

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반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9ed7781179a4f35ba8123f196f25567
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786165B2

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