Lithium hydroxide, monohydrate → HCID 23121814, compound

HRID 2113214Notes

Reaction equation

HRID 2113214 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:31]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=1)[C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]([O:26]C(=O)C)([CH3:25])[CH3:24])=[CH:17][CH:16]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>CO.O.C1COCC1>[CH2:35]([O:34][C:32]1[CH:31]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:33]=1)[C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]([OH:26])([CH3:25])[CH3:24])=[CH:17][CH:16]=1)=[O:13])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 23121800HCID 23121800, compound

Product 1

HCID 23121814HCID 23121814, compoundYield 82.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of N-{6-[(3,5-dibenzyloxybenzoyl)amino]-pyridin-3-yl}-2-acetoxy-2-methyl-propionamide (158 mg) in methanol (10 ml) was added a solution of LiOH.H2O (30 mg) in water (1 ml) and THF (3 ml). The mixture was stirred at ambient temperature for 20 hours. Volatile material was removed by evaporation. To the residue was added water (10 ml). Made acidic with 2M hydrochloric acid. Precipitate filtered off, washed with ethyl acetate, and dried under high vacuum to give the title compound (120 mg) as a solid, 1H NMR δ (d6-DMSO): 1.35 (s, 6H), 5.18 (s, 4H), 6.88 (s, 1H), 7.28 to 7.48 (m, 12H), 8.08 (d, 1H), 8.22 (d, 1H), 8.82 (s, 1H), 9.90 (s, 1H), 10.96 (s, 1H). MS ES+ 512.16 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation
  2. additionTo the residue was added water (10 ml)
  3. filtrationPrecipitate filtered off
  4. washwashed with ethyl acetate
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-e1dbb65266ec403baf47768a504a82c7
Source dataset
uspto-grants-2009_04
Patent number
US07524957B2

Reaction notes

Loading…