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

HRID 29841Notes

Reaction equation

HRID 29841 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.C([O:32][C:33]1[CH:43]=[CH:42][C:36]([CH2:37][C:38]2([NH2:41])[CH2:40][CH2:39]2)=[CH:35][CH:34]=1)C1C=CC=CC=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:41][C:38]2([CH2:37][C:36]3[CH:42]=[CH:43][C:33]([OH:32])=[CH:34][CH:35]=3)[CH2:40][CH2:39]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 84468TrifluoroacetateHCID 231061211-(4-Benzyloxy-benzyl)-cyclopropylamineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 115668905-hydroxy-8-{1-hydroxy-2-[1-(4-hydroxy-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 253 mg (1 mmol) 1-(4-benzyloxy-benzyl)-cyclopropylamine. Yield: 20 mg (4%, trifluoroacetate); mass spectroscopy: [M+H]+=371.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a3590e5729f94d67ac2af19a59c3070f
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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