Pyridine → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-(2,2,2trifluoroethoxy)-3-oxo-1-propenyl]-cyclopropane-carboxylate

HRID 1639425노트

반응식

HRID 1639425 반응식
[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:14])[O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C@H:3]1[C:15]([OH:17])=[O:16].N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.O[C@@H:41]([C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([O:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:45]=1)[C:42]#[N:43]>C(Cl)Cl>[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])=[O:14])[C@H:3]1[C:15]([O:17][C@H:41]([C:42]#[N:43])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([O:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:45]=1)=[O:16]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 13390085(1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid

생성물 1

HCID 13188366(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-(2,2,2trifluoroethoxy)-3-oxo-1-propenyl]-cyclopropane-carboxylate수율 57.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1.3 g of (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2, 2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid, 0.1 ml of pyridine and 15 ml of methylene chloride were mixed with agitation and then 1.05 g of dicyclohexylcarbodiimide were added thereto. A solution of 1.35 g of (S)α-hydroxy-3-phenoxy-benzene-acetonitrile in 5 ml of methylene chloride were then added to the mixture which was stirred for 5 hours at ambient temperature and then was filtered. The filter was rinsed with methylene chloride and 2N hydrochloric acid was added to the filtrate. The decanted organic phase was washed with water, dried and evaporated to dryness. The oil residue was chromatographed over silica gel and was eluted with 95-5 cyclohexane-ethyl acetate mixture to obtain 1.33 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-(2,2,2-trifluoroethoxy)-3-oxo-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+42°±2° (c=0.7% in benzene).

후처리

  1. filtrationwas filtered
  2. washThe filter was rinsed with methylene chloride and 2N hydrochloric acid
  3. additionwas added to the filtrate
  4. washThe decanted organic phase was washed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe oil residue was chromatographed over silica gel
  8. washwas eluted with 95-5 cyclohexane-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-d03faf6c3154454bb5f9840eca8b2830
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04883806

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