Methanol → trans-5-(4-Ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

HRID 1419067Notes

Reaction equation

HRID 1419067 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[C:16]3[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=3[N:14]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:13](=[O:27])[C@@H:12]([CH2:28][C:29]([O:31]CC)=[O:30])[O:11]2)=[C:6]([O:34][CH3:35])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].CO.O1CCCC1>O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[C:16]3[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=3[N:14]([CH2:22][C:23]([CH3:25])([CH3:26])[CH3:24])[C:13](=[O:27])[C@@H:12]([CH2:28][C:29]([OH:31])=[O:30])[O:11]2)=[C:6]([O:34][CH3:35])[CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 67603127Ethyl trans-5-(4-ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate

Product 1

HCID 10140397trans-5-(4-Ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl trans-5-(4-ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (0.18 g), potassium carbonate (0.10 g), methanol (10 ml), tetrahydrofuran (10 ml) and water (5 ml) was refluxed for 1.5 h. The resulting mixture was concentrated in vacuo, acidified with 1N hydrochloric acid (50 ml) and extracted with ethyl acetate (50 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo to give trans-5-(4-ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid as colorless crystals (mp=230°-232° C.).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate (50 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69a7df2ea17847a7a38817f76b847774
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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