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

HRID 229422Notes

Reaction equation

HRID 229422 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][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]2([NH2:38])[CH2:37][CH2:36]2)=[CH:29][CH:28]=1.FC(F)(F)C([O-])=O>>[OH:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([CH:20]([OH:24])[CH2:21][NH:38][C:35]2([CH2:34][CH2:33][C:30]3[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=3)[CH2:37][CH2:36]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-oneHCID 597892441-[2-(4-Methoxyphenyl)ethyl]cyclopropan-1-amine

Product 1

HCID 231060855-hydroxy-8-(1-hydroxy-2-{1-[2-(4-methoxy-phenyl)-ethyl]-cyclopropylamino}-ethyl)-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-[2-(4-methoxy-phenyl)-ethyl]-cyclopropylamine. Yield: 55 mg (11%, trifluoroacetate); mass spectroscopy: [M+H]=399.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f3d6a414c2714a39a32e7de1819e74fe
Source dataset
uspto-grants-2009_07
Patent number
US07563806B2

Reaction notes

Loading…