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

HRID 1194947

Reaction equation

HRID 1194947 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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).

Sources & evidence

ORD record
ord-b74806e46eb14c82a472f13ae452f449
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Linked notes

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