(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]-cyclopropane-carboxylate

HRID 464461

반응식

HRID 464461 반응식
[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[O:8])[C@H:3]1[C:14]([OH:16])=[O:15].[C:18]([C@@H:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)#[N:19]>>[CH3:14][CH2:3][CH2:2][CH2:4][CH2:5][CH3:6].[CH:23]([O:27][CH:28]([CH3:33])[CH3:29])([CH3:24])[CH3:22].[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13]2)=[O:8])[C@H:3]1[C:14]([O:16][C@H:20]([C:18]#[N:19])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1)=[O:15]

참가 물질

4

반응물 2

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 70477467(1R,cis) 2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid

생성물 2

HCID 21881879Diisopropylether hexaneHCID 131713082(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]-cyclopropane-carboxylate수율 178.3%

실험 절차

Using the procedure of Step A above, 1.8 g of the acid of Step B and 2 g of (S)α-cyano-3-phenoxy-benzyl alcohol were reacted and the product was chromatographed over silica gel. Elution with a 9-1 cyclohexane-ethyl acetate mixture and then with an 8-2 n-hexane-isopropyl ether mixture yielded 3.0 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+45.5°±2° (c=0.6% in chloroform).

후처리

  1. customthe product was chromatographed over silica gel
  2. washElution with a 9-1 cyclohexane-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-3dcc9229ad294d1a88625bb0825a4847
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04547522

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