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

HRID 29843Notes

Reaction equation

HRID 29843 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.[CH2:25]([O:27][C:28]1[CH:38]=[CH:37][C:31]([CH2:32][C:33]2([NH2:36])[CH2:35][CH2:34]2)=[CH:30][CH:29]=1)[CH3:26].FC(F)(F)C([O-])=O>>[CH2:25]([O:27][C:28]1[CH:38]=[CH:37][C:31]([CH2:32][C:33]2([NH:36][CH2:21][CH:20]([C:12]3[C:13]4[O:18][CH2:17][C:16](=[O:19])[NH:15][C:14]=4[C:9]([OH:8])=[CH:10][CH:11]=3)[OH:24])[CH2:35][CH2:34]2)=[CH:30][CH:29]=1)[CH3:26]

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231060741-[(4-Ethoxyphenyl)methyl]cyclopropan-1-amineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 597892568-{2-[1-(4-ethoxy-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 191 mg (1 mmol) 1-(4-ethoxy-benzyl)-cyclopropylamine. Yield: 17 mg (3%, trifluoroacetate); mass spectroscopy: [M+H]+=399.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-bfc632a956394ac587dfc7bc14c7c67a
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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