1,1'-Carbonyldiimidazole → rel-(4R,5S)-4,5-bis(3'-benzyloxy-4'-methoxyphenyl)oxazolidin-2-one

HRID 327338Notes

Reaction equation

HRID 327338 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@H:17]([OH:36])[C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:21]=2)[NH2:19])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37](N1C=CN=C1)(N1C=CN=C1)=[O:38]>C1(C)C=CC=CC=1>[CH2:29]([O:28][C:22]1[CH:21]=[C:20]([C@@H:18]2[C@H:17]([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[O:36][C:37](=[O:38])[NH:19]2)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22849455rel-(1S,2R)-1,2-bis(3'-Benzyloxy-4'-methoxyphenyl)-2-aminoethanol

Product 1

HCID 15011034rel-(4R,5S)-4,5-bis(3'-benzyloxy-4'-methoxyphenyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Mixture: 1.0 g (2.06 mmol) of rel-(1S,2R)-1,2-bis(3'-benzyloxy-4'-methoxyphenyl)-2-aminoethanol, 334 mg (2.05 mmol) of carbonyldiimidazole, 20 ml of toluene.

Sources & evidence

ORD record
ord-7c245ae600964402b67dc6817f5de098
Source dataset
uspto-grants-1993_12
Patent number
US05272270

Reaction notes

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