Dimethylformamide → tert-butyl (2R)-2-[(2R)-4-(4-chlorophenyl)-3-oxomorpholin-2-yl]-2-hydroxyacetate

HRID 876583Notes

Reaction equation

HRID 876583 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([N:6]([C:10](=[O:22])[C@H:11]([OH:21])[C@@H:12]([OH:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:8]Cl)=[CH:4][CH:3]=1.CN(C=O)C>CC(O)(C)C.CS(C)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([N:6]2[CH2:7][CH2:8][O:21][C@H:11]([C@@H:12]([OH:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10]2=[O:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 67223250tert-butyl (2R,3R)-4-[4-chloro-N-(2-chloroethyl)anilino]-2,3-dihydroxy-4-oxobutanoate

Product 1

HCID 67222627tert-butyl (2R)-2-[(2R)-4-(4-chlorophenyl)-3-oxomorpholin-2-yl]-2-hydroxyacetateYield 24.9%

Reagents, catalysts & solvents 1

HCID 86634320DMSO t-BuOHSolvent

Procedure

According to the Step 7-5 in synthetic method for EXAMPLE 7, compound 60-4 (1.78 g) and DMF were used instead of 7-4 and t-BuOH-DMSO to obtain compound 60-5 (400 mg) as a pale yellow amorphous solid.

Sources & evidence

ORD record
ord-1f622ecd6ab84a8e9fa7a4930cc1304f
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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