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

HRID 29832Notes

Reaction equation

HRID 29832 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]([F:39])([F:38])[C:27]1[CH:37]=[CH:36][C:30]([CH2:31][C:32]2([NH2:35])[CH2:34][CH2:33]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:35][C:32]2([CH2:31][C:30]3[CH:36]=[CH:37][C:27]([C:26]([F:25])([F:38])[F:39])=[CH:28][CH:29]=3)[CH2:33][CH2:34]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231061381-(4-Trifluoromethylbenzyl)cyclopropylamineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 231061115-hydroxy-8-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-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 215 mg (1 mmol) 1-(4-trifluoromethyl-benzyl)-cyclopropylamine. Yield: 18 mg (3%, trifluoroacetate); mass spectroscopy: [M+H]+=423.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-46a278d667c149c28822cdc6b5cf4619
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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