Trifluoroacetate → 5-hydroxy-8-{1-hydroxy-2-[1-(2,4,6-trimethyl-benzyl)-cyclopropylamino]-ethyl}-4H-benzo[1,4]oxazin-3-one

HRID 29845Notes

Reaction equation

HRID 29845 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:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:27]=1[CH2:28][C:29]1([NH2:32])[CH2:31][CH2:30]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:32][C:29]2([CH2:28][C:27]3[C:33]([CH3:38])=[CH:34][C:35]([CH3:37])=[CH:36][C:26]=3[CH3:25])[CH2:31][CH2:30]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 23106134HCID 23106134, compoundHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 231061315-hydroxy-8-{1-hydroxy-2-[1-(2,4,6-trimethyl-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 189 mg (1 mmol) 1-(2,4,6-trimethyl-benzyl)-cyclopropylamine. Yield: 26 mg (5%, trifluoroacetate); mass spectroscopy: [M+H]+=397.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6bc57e41fe1f4ad99d2acf81d2b8bb4d
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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