Lithium Hydroxide → HCID 178427487, compound

HRID 840789Notes

Reaction equation

HRID 840789 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C@@H:9]([CH2:23][CH2:24][C:25]([NH:27][CH2:28][NH:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[NH:26])[C:8]1=[O:40])=[O:5])C.[Li+].[OH-]>C1COCC1>[CH2:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:4]([OH:5])=[O:3])[C:8](=[O:40])[C@@H:9]1[CH2:23][CH2:24][C:25]([NH:27][CH2:28][NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)(=[O:32])=[O:31])=[NH:26])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178472630HCID 178472630, compound

Product 1

HCID 178427487HCID 178427487, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of Example 11 (185 mg, 0.32 mmol) in THF (2 mL) was treated with 2 N LiOH (0.32 mL, 0.64 mmol). The mixture was stirred at room temperature for two and one-half hours. The organic solvent was evaporated in vacuo. The aqueous layer was extracted with EtOAc to remove organic impurities and acidified to pH 2-3 with 2N aq HCl at 0° C. The acidified aqueous layer was extracted with EtOAc and the organic layer was dried over Na2SO4 and evaporated to give the title compound as a white solid (149 mg).

Workup

  1. customThe organic solvent was evaporated in vacuo
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customto remove organic impurities
  4. customacidified to pH 2-3 with 2N aq HCl at 0° C
  5. extractionThe acidified aqueous layer was extracted with EtOAc
  6. dry with materialthe organic layer was dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-e11c8e6492f247ccb30a6ff5270a649c
Source dataset
uspto-grants-2002_04
Patent number
US06369063B1

Reaction notes

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