Triphenylphosphine → HCID 178472882, compound

HRID 1194926Notes

Reaction equation

HRID 1194926 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:32]/[OH:33])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:53][C@H:54]1[CH2:59][CH2:58][C@H:57](O)[CH2:56][CH2:55]1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:32]/[O:33][C@H:57]2[CH2:58][CH2:59][C@@H:54]([Cl:53])[CH2:55][CH2:56]2)/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetateHCID 178521565HCID 178521565, compound

Product 1

HCID 178472882HCID 178472882, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(hydroxyimino)acetate (0.91 g), triphenylphosphine (0.58 g) and trans-4-chlorocyclohexanol (0.54 g) were dissolved together in anhydrous benzene (20 ml). Diethyl azodicarboxylate (0 35 ml) was added and the solution heated at reflux for 16 h with exclusion of moisture. Evaporation of solvent followed by chromatography afforded the title compound as a near colourless gum (225 mg, 20%); νmax (KBr) 1737, 1595 (w), 1529, 1491 and 1446 cm-1 ; δHH (CDCl3) 1.39 (3H, t, J 7 Hz), 1.69, 1.96 and 2.06 (8H, 3m), 4.04 (1H, qt, J 6 Hz), 4.39(2H, q, J 7Hz), 4.44 (1H, qt, J 3 Hz), 6.49 (1H, s), 6.97 (1H, brs, D2O exch), and 7.32 (15H, s). [Mass spectrum: +ve ion (thioglycerol) MH+ (574), MNa+ (596)].

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 16 h with exclusion of moisture
  3. customEvaporation of solvent

Sources & evidence

ORD record
ord-7bd01a13ca2b4da2ad41a69ef06e4478
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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