Lithium Hydroxide → HCID 18689654, compound

HRID 1872265Notes

Reaction equation

HRID 1872265 reaction equation
C([O:8][C:9]([CH:11]1[CH2:17][CH:16]=[CH:15][CH2:14][N:13]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:12]1[C:29](=[O:45])[NH:30][O:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=O)C1C=CC=CC=1.[Li+].[OH-]>C1COCC1.O>[CH:32]([O:31][N:30]1[C:9](=[O:8])[CH:11]2[CH:12]([N:13]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH2:14][CH:15]=[CH:16][CH2:17]2)[C:29]1=[O:45])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 53922354HCID 53922354, compound

Product 1

HCID 18689654HCID 18689654, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The 2-benzhydryloxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-3-carboxylic acid benzyl ester (430 mg, 0.69 mmoL) was dissolved in a THF:H2O (1:1, 10 mL) mixture and was then treated with LiOH (35 mg, 0.82 mmoL). This solution was stirred overnight at ambient temperature. The THF was removed in vacuo and the resulting mixture was acidified with 2 M aqueous citric acid. The product was extracted into diethyl ether, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 10% methanol in chloroform) to give 7-benzhydryloxy-1-(4-methoxybenzenesulfonyl)-2,5,5a,8a-tetrahydro-1H-pyrrolo[3,4-b]azepine-6,8-dione; MS: (M+H)+ 519.

Workup

  1. customThe THF was removed in vacuo
  2. extractionThe product was extracted into diethyl ether
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (silica, 10% methanol in chloroform)

Sources & evidence

ORD record
ord-c4129b0af0aa406699006225b9503269
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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