Lithium hydroxide, monohydrate → HCID 23121814, compound

HRID 133694Notes

Reaction equation

HRID 133694 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-f0d344a664f4416680ca769b45fc7adb
Source dataset
uspto-grants-2008_06
Patent number
US07390908B2

Reaction notes

Loading…