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

HRID 29844Notes

Reaction equation

HRID 29844 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.[CH2:25]([O:29][C:30]1[CH:40]=[CH:39][C:33]([CH2:34][C:35]2([NH2:38])[CH2:37][CH2:36]2)=[CH:32][CH:31]=1)[CH2:26][CH2:27][CH3:28].FC(F)(F)C([O-])=O>>[CH2:25]([O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:34][C:35]2([NH:38][CH2:21][CH:20]([C:12]3[C:13]4[O:18][CH2:17][C:16](=[O:19])[NH:15][C:14]=4[C:9]([OH:8])=[CH:10][CH:11]=3)[OH:24])[CH2:37][CH2:36]2)=[CH:39][CH:40]=1)[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231061441-(4-Butoxy-benzyl)-cyclopropylamineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 597892588-{2-[1-(4-butoxy-benzyl)-cyclopropylamino]-1-hydroxy-ethyl}-5-hydroxy-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 219 mg (1 mmol) 1-(4-butoxy-benzyl)-cyclopropylamine. Yield: 107 mg (20%, trifluoroacetate); mass spectroscopy: [M+H]+=427.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-405c99c585494611a8e2d6364c36c200
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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