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

HRID 29829Notes

Reaction equation

HRID 29829 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][CH:36]=1)[CH2:29][C:30]1([NH2:33])[CH2:32][CH2:31]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:33][C:30]2([CH2:29][C:28]3[CH:34]=[CH:35][CH:36]=[C:26]([CH3:25])[CH:27]=3)[CH2:32][CH2:31]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231060771-(3-Methylbenzyl)cyclopropanamineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 231061475-hydroxy-8-{1-hydroxy-2-[1-(3-methyl-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 161 mg (1 mmol) 1-(3-methyl-benzyl)-cyclopropylamine. Yield: 179 mg (37%, trifluoroacetate); mass spectroscopy: [M+H]+=369.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-42e019db59b24367abefea06ead1a594
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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