Hydrochloric Acid → 4-[(3-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-(methyloxy)benzoic acid

HRID 222749Notes

Reaction equation

HRID 222749 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][C:4]=1[O:13][C:14]1[CH:31]=[CH:30][C:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22][C:16]=2[CH:15]=1.[OH-].[Na+].Cl>C(O)C>[CH3:29][C:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][C:17]2[CH:30]=[CH:31][C:14]([O:13][C:4]3[CH:5]=[CH:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:3]=3[O:2][CH3:1])=[CH:15][C:16]=2[CH2:22][CH2:21]1)=[O:24])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 574402971,1-Dimethylethyl 7-({2-(methyloxy)-4-[(methyloxy)carbonyl]phenyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 574402984-[(3-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-(methyloxy)benzoic acidYield 64.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,1-Dimethylethyl 7-({2-(methyloxy)-4-[(methyloxy)carbonyl]phenyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (E264, Step 3) (240 mg, 0.56 mmol) was dissolved in ethanol (2 ml), treated with 2M sodium hydroxide (1 ml) and the resulting mixture was stirred for 1.5 hours. The mixture was acidified with 2M hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated in vacuo to afford the title compound (0.15 g); MS (ES+) m/e 314 [(M+H)—CO2tBu]+.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried under magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-8d4b9287798d4c728379cbf299320441
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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