Ethylene Oxide → rel-(4R,5S)-4,5-bis(3'-Benzyloxy-4'-methoxyphenyl)-3-(2'-hydroxyethyl)oxazolidine-2-one

HRID 327339

Reaction equation

HRID 327339 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:17]2[C@H:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:23]=3)[O:20][C:19](=[O:38])[NH:18]2)[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.[CH2:39]1[O:41][CH2:40]1.[Cl-].C[NH3+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:17]2[C@H:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:23]=3)[O:20][C:19](=[O:38])[N:18]2[CH2:39][CH2:40][OH:41])[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

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 11637Methanamine, hydrochloride (1:1)HCID 15011034rel-(4R,5S)-4,5-bis(3'-benzyloxy-4'-methoxyphenyl)oxazolidin-2-one

Product 1

HCID 15011035rel-(4R,5S)-4,5-bis(3'-Benzyloxy-4'-methoxyphenyl)-3-(2'-hydroxyethyl)oxazolidine-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mixture: 100 mg of rel-(4R,5S)-4,5-bis(3'-benzyloxy-4'-methoxyphenyl)oxazolidin-2-one, 5 ml of ethylene oxide, 15 ml of tetrahydrofuran, 5 mg of methylammonium chloride.

Sources & evidence

ORD record
ord-de698e6da9e241918f4e5e07888b6435
Source dataset
uspto-grants-1993_12
Patent number
US05272270

Linked notes

Loading…