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

HRID 29825
Notes
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Reaction equation

HRID 29825 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][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]([O:26][CH3:25])=[CH:28][CH:29]=3)[CH2:34][CH2:33]2)=[CH:11][CH:10]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231060921-(4-Methoxybenzyl)cyclopropanamineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 116895235-hydroxy-8-{1-hydroxy-2-[1-(4-methoxy-benzyl)-cyclopropylamino]-ethyl}-4H-benzo[1,4]oxazin-3-one

Procedure

Reaction of 329 mg (1 mmol) 5-benzyloxy-8-(2,2-dihydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 177 mg (1 mmol) 1-(4-methoxy-benzyl)-cyclopropylamine according to general method 3. Yield: 39 mg (8%, trifluoroacetate); mass spectroscopy: [M+H]+=385.

Sources & evidence

ORD record
ord-7e2a402128f04bb184dac64ae54acecb
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07423035B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes