Lithium hydroxide, monohydrate → HCID 10432784, compound

HRID 2253737Notes

Reaction equation

HRID 2253737 reaction equation
[CH3:1][N:2]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7](/[CH:19]=[CH:20]\[C:21]([O:23]C)=[O:22])[CH:6]=1.O[Li].O>CO.C1COCC1.O>[CH3:1][N:2]([CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7](/[CH:19]=[CH:20]\[C:21]([OH:23])=[O:22])[CH:6]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10646909HCID 10646909, compound

Product 1

HCID 10432784HCID 10432784, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 160 mg (0.36 mmoles) of cis-N-methyl-N-phenethyl-2-[4-benzyloxy-3-(2-carbomethoxyvinyl)phenyl]acetamide in 10 ml of a 1:1:1 MeOH/THF/H2O mixture at 0° C. is added 76 mg (1.8 mmoles) of LiOH·H2O. The reaction mixture is allowed to come to room temperature and stirred at room temperatured for 12 hours after which time the eraction mixtured is concentrated down in vacuo, taken up in H2O washed with ether (2 times) and acidified to pH 3-4 with 1N HCl. The aqueous layer extracted with ether (2 times). The ether extracts are combined and are dried with MgSO4, filtered and concentrated down in vacuo to give cis-N-methyl-N-phenethyl-2-[4-benzyloxy-3-(2-carboxyvinyl)phenyl]acetamide. (m.p. 48°-51° C.)

Workup

  1. customto come to room temperature
  2. concentrationafter which time the eraction mixtured is concentrated down in vacuo
  3. washwashed with ether (2 times)
  4. extractionThe aqueous layer extracted with ether (2 times)
  5. dry with materialare dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down in vacuo

Sources & evidence

ORD record
ord-b5022d1d9de14f50b7af52308e4e169f
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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