2-Thiophenecarbonyl chloride → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-[2-(thien-2-yl-carbonylamino)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 2413408Notes

Reaction equation

HRID 2413408 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]2[CH2:14][S:13][CH:12]3[N:9]([C:10](=[O:23])[CH:11]3[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]=2[C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[CH:5][N:6]=1.Cl[C:41]([C:43]1[S:44][CH:45]=[CH:46][CH:47]=1)=[O:42]>C(N(CC)CC)C>[CH:27]([O:26][C:24]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[C:4]1[S:3][C:2]([NH:1][C:41]([C:43]3[S:44][CH:45]=[CH:46][CH:47]=3)=[O:42])=[N:6][CH:5]=1)[CH:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]2=[O:23])=[O:25])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 131759453-(2-Aminothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 204304222-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-[2-(thien-2-yl-carbonylamino)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 85.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 2, starting from 3-(2-amino-thiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (4.5 g), triethylamine (1.23 cc) and 2-chlorocarbonyl-thiophene (1.4 g), 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-[2-(thien-2-yl-carbonylamino)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (4.62 g) is obtained, in the form of a cream-coloured powder, after purification over Merck silica gel (0.06-0.2 mm).

Sources & evidence

ORD record
ord-a4342636e9194bc4b897cd140e2c3a53
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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