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

HRID 1991339Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl (2R)-3-[(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)amino]-2-hydroxypropanoate (Step 8, 0.84 g, 2.96 mmol) and 1,1′-carbonyldiimidazole (0.48 g, 2.96 mmol) in acetonitrile is stirred and heated at 60° C. overnight. The reaction is diluted with ethyl acetate, washed with 2N HCl and saline, and evaporated under reduced pressure. The resulting solid is triturated with methanol to give pure product as a white solid (0.88 g, 96%); MS for C13H11FN2O6 m/z 311 (M+H)+.

Workup

washwashed with 2N HCl and saline
customevaporated under reduced pressure
customThe resulting solid is triturated with methanol

Sources & evidence

ORD record: ord-35eef69897af409cac61043733fe01e6
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645781B2

Reaction notes

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