4-Methoxybenzyl alcohol → Methyl 3-(2,2,2-trichloroethoxycarbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate

HRID 616156Notes

Reaction equation

HRID 616156 reaction equation
COC1C=CC(CO)=CC=1.CC1(C)C2(C)C(O)CC1CC2.[Cl:22][C:23]([Cl:27])([Cl:26])[CH2:24][OH:25].COC1C=CC(C[O:35][C:36]([NH:38][CH:39]2[C:42](=[O:43])[N:41]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=3[O:53][CH3:54])[CH:40]2[C:55]([O:57][CH3:58])=[O:56])=O)=CC=1.C(OC(NC1C(=O)N(CC2C=CC(OC)=CC=2OC)C1C(OC)=O)=O)C1C=CC=CC=1>C(O)(C)(C)C>[Cl:22][C:23]([Cl:27])([Cl:26])[CH2:24][O:25][C:36]([NH:38][CH:39]1[C:42](=[O:43])[N:41]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=2[O:53][CH3:54])[CH:40]1[C:55]([O:57][CH3:58])=[O:56])=[O:35]

Participants

7

Reactant 5

HCID 77384-Methoxybenzyl alcoholHCID 8259TrichloroethanolHCID 64685BorneolHCID 13470810Methyl 3-(benzyloxycarbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylateHCID 23470086Methyl 3-(p-methoxybenzyloxycarbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate

Product 1

HCID 14230565Methyl 3-(2,2,2-trichloroethoxycarbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

When p-methoxybenzyl alcohol, isoborneol, benzy, alcohol, or 2,2,2-trichloroethanol is substituted for t-butanol in Example 3, methyl 3-(p-methoxybenzyloxy-carbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate, methyl 3-(isobornyloxycarbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate, methyl 3-(benzyloxycarbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate., or methyl 3-(2,2,2-trichloroethoxycarbonylamino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate is obtained

Sources & evidence

ORD record
ord-ff086200b4f44e72bfe3ee787bc74f89
Source dataset
uspto-grants-1978_02
Patent number
US04072674

Reaction notes

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