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Hydrochloric Acid → 8,8-Difluoro-3-(4'-fluoro-4-methylbiphenyl-3-yl)-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

HRID 1841899
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HRID 1841899 반응식
[F:1][C:2]1([F:30])[CH2:7][CH2:6][C:5]([NH:12][C:13](=[O:29])[CH2:14][C:15]2[CH:16]=[C:17]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:18]=[CH:19][C:20]=2[CH3:21])([C:8](OC)=[O:9])[CH2:4][CH2:3]1.CN(C)C(=O)C.CC(C)([O-])C.[K+].Cl>O>[F:30][C:2]1([F:1])[CH2:7][CH2:6][C:5]2([NH:12][C:13](=[O:29])[C:14]([C:15]3[CH:16]=[C:17]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH:18]=[CH:19][C:20]=3[CH3:21])=[C:8]2[OH:9])[CH2:4][CH2:3]1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 31374Dimethylacetamide2회HCID 23665647Potassium tert-butoxideHCID 68283296Methyl 4,4-difluoro-1-{[(4'-fluoro-4-methylbiphenyl-3-yl)acetyl]amino}cyclohexanecarboxylate

생성물 1

HCID 601684118,8-Difluoro-3-(4'-fluoro-4-methylbiphenyl-3-yl)-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2.80 g (5.94 mmol) of the compound from Example 7A were initially charged in a solution of 8 ml of DMA (N,N-dimethylacetamide), a solution of 5 ml of DMA and 1.75 g (2.5 eq.) of potassium tert-butoxide was added dropwise at 20° C. and the mixture was stirred at room temperature for 4 h. The mixture was poured into 200 ml of water and the reaction was adjusted to pH 2 using concentrated aqueous hydrochloric acid, and the resulting residue was filtered off with suction. Purification by flash column chromatography (silica gel; ethyl acetate/n-hexane 1:1) gave 1.07 g (44% of theory) of the title compound.

후처리

  1. filtrationthe resulting residue was filtered off with suction
  2. customPurification by flash column chromatography (silica gel; ethyl acetate/n-hexane 1:1)

출처 및 근거

ORD 기록
ord-f0c18b8a86a34e51ad1a36a4a3bf9cda
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946124B2

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