Acetic Acid → 5-benzyloxy-8-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 969471Notes

Reaction equation

HRID 969471 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[C:16]2[NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[O:20][C:15]=2[C:14]([CH:24]([OH:39])[CH:25]=[N:26][C:27]([CH3:38])([CH3:37])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC(C)=O.C(O)(=O)C>C(O)C.O>[CH2:3]([O:10][C:11]1[C:16]2[NH:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:22])[O:20][C:15]=2[C:14]([CH:24]([OH:39])[CH2:25][NH:26][C:27]([CH3:38])([CH3:37])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 4311764Sodium borohydrideHCID 694612895-benzyloxy-8-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylimino]-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 694590295-benzyloxy-8-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.6 g sodium borohydride are added at ambient temperature to a solution of 8.6 g (17 mmol) 5-benzyloxy-8-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylimino]-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one in 80 mL ethanol and the mixture is stirred for one hour. The reaction mixture is combined with 20 mL acetone, stirred for 30 minutes, diluted with 50 ml of water and acidified with glacial acetic acid. After the organic solvents have been distilled off ethyl acetate is added to the aqueous residue. It is acidified with conc. hydrochloric acid and diluted with diethyl ether. The product precipitated as the hydrochloride is suction filtered and washed with acetone and diethyl ether. Yield: 8.4 g (91%, hydrochloride); melting range=215-218° C.

Workup

  1. stirringstirred for 30 minutes
  2. distillationAfter the organic solvents have been distilled off ethyl acetate
  3. additionis added to the aqueous residue
  4. additiondiluted with diethyl ether
  5. customThe product precipitated as the hydrochloride
  6. filtrationfiltered
  7. washwashed with acetone and diethyl ether

Sources & evidence

ORD record
ord-0ba7c6ab4dd948229f828d2d18646372
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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