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

HRID 29828Notes

Reaction equation

HRID 29828 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.[CH3:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[CH3:37])[CH2:29][C:30]1([NH2:33])[CH2:32][CH2:31]1.FC(F)(F)C([O-])=O>>[CH3:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[CH3:37])[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])[CH2:31][CH2:32]1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231061461-[(3,4-Dimethylphenyl)methyl]cyclopropan-1-amineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 597892438-{2-[1-(3,4-dimethyl-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 175 mg (1 mmol) 1-(3,4-dimethyl-benzyl)-cyclopropylamine. Yield: 233 mg (47%, trifluoroacetate); mass spectroscopy: [M+H]+=383.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-55eb3a38fc9044b8b915e51da98a6eca
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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