4-Chlorobenzyl alcohol → (3S,2RS) 3-Allyloxycarbonylamino-2-(4-chlorobenzyl)oxy-5-oxotetrahydrofuran

HRID 2230476Notes

Reaction equation

HRID 2230476 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]1[CH2:12][C:11](=[O:13])[O:10][CH:9]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:6])[CH:2]=[CH2:3].[Cl:22]C1C=CC(CO)=CC=1>>[CH2:1]([O:4][C:5]([NH:7][C@H:8]1[CH2:12][C:11](=[O:13])[O:10][CH:9]1[O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 133974-Chlorobenzyl alcoholHCID 10989944(3S,2RS)3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuran

Product 1

HCID 59947520(3S,2RS) 3-Allyloxycarbonylamino-2-(4-chlorobenzyl)oxy-5-oxotetrahydrofuran

Procedure

was synthesized from allyloxycarbonylamino-β-tert-butyl aspartate by the methods employed by Chapman (Bioorg. & Med. Chem. Lett., 2, pp.6.15-6.18 (1992)) to prepare (3S,2RS)3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuran using 4-chlorobenzyl alcohol instead of benzyl alcohol to afford 1.84 g of 2101a as a crystalline solid.

Sources & evidence

ORD record
ord-ae03ebf46e824b15941dba057077b0f1
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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