1,1'-Carbonyldiimidazole → methyl(5R)-3-(4-fluoro-3-isopropyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

HRID 1991349Notes

Reaction equation

HRID 1991349 reaction equation
[F:1][C:2]1[C:7]2[N:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=[C:4]([NH:15][CH2:16][C@@H:17]([OH:22])[C:18]([O:20][CH3:21])=[O:19])[CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>>[F:1][C:2]1[C:7]2[N:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=[C:4]([N:15]2[CH2:16][C@H:17]([C:18]([O:20][CH3:21])=[O:19])[O:22][C:23]2=[O:24])[CH:3]=1

Participants

3

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86610082methyl (2R)-3-[(4-fluoro-3-isopropyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate

Product 1

HCID 68492587methyl(5R)-3-(4-fluoro-3-isopropyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

Procedure

Prepared from methyl (2R)-3-[(4-fluoro-3-isopropyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate (Step 3, 0.908 g, 2.91 mmol) and 1,1′-carbonyldiimidazole (0.471 g, 2.91 mmol) according to the method of EXAMPLE 86, Step 9 (0.90 g, 92%); MS for C15H15FN2O6 m/z 339 (M+H)+.

Sources & evidence

ORD record
ord-ee3fe2b9d06a4603ae7eb7f3cd418a5f
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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