Lithium Hydroxide → HCID 86629246, compound

HRID 1677620Notes

Reaction equation

HRID 1677620 reaction equation
C[O:2][C:3](=[O:48])[CH:4]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:31]([NH2:40])=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:25]=1)[O:5][P:6]([CH:9]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH:10]([CH3:12])[CH3:11])([OH:8])=[O:7].[Li+].[OH-].OS([O-])(=O)=O.[Na+]>CO.O>[C:44]([O:43][C:41]([N:30]([C:26]1[CH:25]=[C:24]([CH:4]([O:5][P:6]([CH:9]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH:10]([CH3:12])[CH3:11])([OH:8])=[O:7])[C:3]([OH:48])=[O:2])[CH:29]=[CH:28][CH:27]=1)[C:31]([NH2:40])=[N:32][C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])=[O:42])([CH3:46])([CH3:47])[CH3:45]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 86629247HCID 86629247, compound

Product 1

HCID 86629246HCID 86629246, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a slurry of 2-(3-(N,N′-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid methyl ester in 10 mL of MeOH and 5 mL of H2O was added LiOH (411.9 mg, 9.82 mmol). After stirring the cloudy yellow solution for 2 hours, the reaction was acidified to pH 2 with 1M NaHSO4 and extracted with CH2Cl2 (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give 2-(3-(N,N′-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-(benzyloxycarbonyl)amino-2-methylpropyl)-(hydroxy)phosphinoyloxy)ethanoic acid as a yellow oil that was used without further purification.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-838b2c0cf68547dab33a59dae37534e9
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

Loading…