Trifluoroacetate → 8-{2-[1-(3,5-difluoro-benzyl)-cyclopropylamino]-1-hydroxy-ethyl}-5-hydroxy-4H-benzo[1,4]oxazin-3-one

HRID 29830Notes

Reaction equation

HRID 29830 reaction equation
C([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([C:20](=[O:24])[CH:21](O)O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[F:25][C:26]1[CH:27]=[C:28]([CH:34]=[C:35]([F:37])[CH:36]=1)[CH2:29][C:30]1([NH2:33])[CH2:32][CH2:31]1.FC(F)(F)C([O-])=O>>[F:25][C:26]1[CH:27]=[C:28]([CH:34]=[C:35]([F:37])[CH:36]=1)[CH2:29][C:30]1([NH:33][CH2:21][CH:20]([C:12]2[C:13]3[O:18][CH2:17][C:16](=[O:19])[NH:15][C:14]=3[C:9]([OH:8])=[CH:10][CH:11]=2)[OH:24])[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231060931-(3,5-Difluorobenzyl)cyclopropan-1-amineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 116539848-{2-[1-(3,5-difluoro-benzyl)-cyclopropylamino]-1-hydroxy-ethyl}-5-hydroxy-4H-benzo[1,4]oxazin-3-one

Procedure

Prepared according to general method 3 from 329 mg (1 mmol) 5-benzyloxy-8-(2,2-dihydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 183 mg (1 mmol) 1-(3,5-difluoro-benzyl)-cyclopropylamine. Yield: 66 mg (13%, trifluoroacetate); mass spectroscopy: [M+H]+=391.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ca79575adb784945b39270cf7be20602
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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