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

HRID 29833Notes

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:37]=[CH:36][CH:35]=[CH:34][C:28]=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]=[CH:37][C:27]=3[O:26][CH3:25])[CH2:32][CH2:31]2)=[CH:11][CH:10]=1

Participants

Reactant 3

HCID 84468Trifluoroacetate

HCID 231061021-(2-Methoxybenzyl)cyclopropanamine

HCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 231060965-hydroxy-8-{1-hydroxy-2-[1-(2-methoxy-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 177 mg (1 mmol) 1-(2-methoxy-benzyl)-cyclopropylamine. Yield: 100 mg (20%, trifluoroacetate); mass spectroscopy: [M+H]+=385.

Workup

customPrepared

Sources & evidence

ORD record: ord-13840ed1e5a74d3ebdf74e6f680a9e7f
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423035B2

Reaction notes

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