Triphenylphosphine → HCID 140352849, compound

HRID 1194945Notes

Reaction equation

HRID 1194945 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O/[N:29]=[C:30](/[C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)\[C:31]([O:33][CH2:34][CH3:35])=[O:32].N(C(OC)=O)=NC(OC)=O>C1C=CC=CC=1>[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([O:8]/[N:29]=[C:30](/[C:36]2[N:37]=[C:38]([NH:41][C:42]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[S:39][CH:40]=2)\[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetateHCID 1380828822428-85-9

Product 1

HCID 140352849HCID 140352849, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Methylenecyclohexanol (412 mg), triphenylphosphine (860 mg), and ethyl (Z)-2-hydroxyimino-2-(2-tritylaminothiazol-4-yl)acetate (1.37 g) were dissolved together in anhydrous benzene (9 ml). Dimethyl azodicarboxylate (0.40 ml) was added slowly with stirring and the resulting orange solution was stored at room temperature for 65 h with exclusion of moisture. Workup and chromatography as in example 4a, method 3 afforded the title compound (174 mg), δH (CDCl3) 1.33 (3H, t, J 7 Hz), 1.82, 2.08 and 2.31 (8H, 3m), 4.35 (2H, q, J 7 Hz), 4.51 (1H, m), 4.63 (2H, s), 6.48 (1H, s), 6.96 (1H, br s, D2O exch.), and 7.30 (15H, s).

Sources & evidence

ORD record
ord-5304bb80168b4ec79145b98ad8b93c1d
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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