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

HRID 896208Notes

Reaction equation

HRID 896208 reaction equation
[CH2:1]([N:3]1[C:7]2[C:8]([F:20])=[CH:9][C:10]([NH:12][CH2:13][C@@H:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:6]=2[O:5][C:4]1=[O:21])[CH3:2].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>>[CH2:1]([N:3]1[C:7]2[C:8]([F:20])=[CH:9][C:10]([N:12]3[CH2:13][C@H:14]([C:15]([O:17][CH3:18])=[O:16])[O:19][C:22]3=[O:23])=[CH:11][C:6]=2[O:5][C:4]1=[O:21])[CH3:2]

Participants

3

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86610081methyl (2R)-3-[(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate

Product 1

HCID 68490621methyl(5R)-3-(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

Procedure

Prepared from methyl (2R)-3-[(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate (Step 3, 1.01 g, 3.39 mmol) and 1,1′-carbonyldiimidazole (0.549 g, 3.39 mmol) according to the method of EXAMPLE 86, Step 9 (1.10 g, 99%); MS for C14H13FN2O6 m/z 325 (M+H)+.

Sources & evidence

ORD record
ord-191347d667804aed8c9b84027ff9beba
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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