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

HRID 876582Notes

Reaction equation

HRID 876582 reaction equation
Cl[CH2:2][CH2:3][N:4]([C:12](=[O:24])[C@H:13]([OH:23])[C@@H:14]([OH:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.CN(C=O)C>CC(O)(C)C.CS(C)=O>[F:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]2[CH2:3][CH2:2][O:23][C@H:13]([C@@H:14]([OH:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]2=[O:24])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 67221977tert-butyl (2R,3R)-4-[N-(2-chloroethyl)-4-fluoroanilino]-2,3-dihydroxy-4-oxobutanoate

Product 1

HCID 58181490tert-butyl (2R)-2-[(2R)-4-(4-fluorophenyl)-3-oxomorpholin-2-yl]-2-hydroxyacetateYield 27.5%

Reagents, catalysts & solvents 1

HCID 86634320DMSO t-BuOHSolvent

Procedure

According to the Step 7-5 in synthetic method for EXAMPLE 7, compound 59-4 (1.62 g) and DMF were used instead of 7-4 and t-BuOH-DMSO to obtain compound 59-5 (400 mg) as a colorless amorphous solid.

Sources & evidence

ORD record
ord-051ac5360bc24472b03b4f9b09530ed9
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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