Triphenylphosphine → ethyl (2Z)-2-(4-oxocyclohexyl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

HRID 1194947

반응식

HRID 1194947 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[C:9]([NH:28][C:29]1[S:30][CH:31]=[C:32](/[C:34](=[N:40]/O)/[C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:33]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC)=O)=NC(OC)=O.[K+].[Br-]>C1C=CC=CC=1>[C:9]([NH:28][C:29]1[S:30][CH:31]=[C:32](/[C:34](=[N:40]/[O:8][CH:5]2[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]2)/[C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:33]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 5

HCID 11776TriphenylphosphineHCID 253877Potassium BromideHCID 351621Azodicarboxylic acid dimethyl esterHCID 5437064-HydroxycyclohexanoneHCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate

생성물 1

HCID 88627796ethyl (2Z)-2-(4-oxocyclohexyl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

4-Hydroxycyclohexanone (570 mg; J. B. Aldersley, G. N. Burkhardt, A. E. Gillam, and N. C. Hindley, J. Chem. Soc., 1940, 10) ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate (1.37 g) and triphenyl-phosphine (860 mg) in anhydrous benzene (9 ml) were allowed to react with dimethyl azodicarboxylate (0.40 ml) as described in Example 67c except the reaction time was 14 days. Workup and chromatography gave the title compound (158 mg), νmax (KBr) 3390, 1737, 1710, 1596, 1585, 1529, and 1491cm-1 ; δH (CDCl3) 1.33 (3H, t, J 7Hz), 2.01, 2.31, and 2.55 (8H, 3m), 4.36 (2H, q, J 7z), 4.73 (1H, m), 6.52 (1H, s), 6.97 (1H, brs, D2O exch.), and 7.30 (15H, br s).

출처 및 근거

ORD 기록
ord-b74806e46eb14c82a472f13ae452f449
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04816452

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