Lithium Hydroxide → HCID 178455694, compound

HRID 505635Notes

Reaction equation

HRID 505635 reaction equation
C([O:3][C:4]([C@@:6]1([NH:11][C:12]([CH:14]2[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C:16]3=[CH:27][NH:28][N:29]=[C:15]23)=[O:13])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])C.[Li+].[OH-]>C1COCC1>[C:23]([O:22][C:20]([N:18]1[CH2:19][CH:14]([C:12]([NH:11][C@:6]2([C:4]([OH:5])=[O:3])[CH2:8][C@H:7]2[CH:9]=[CH2:10])=[O:13])[C:15]2=[N:29][NH:28][CH:27]=[C:16]2[CH2:17]1)=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178455695HCID 178455695, compound

Product 1

HCID 178455694HCID 178455694, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl ester 7b (80.0 mg, 0.198 mmol) in THF (1.5 mL) was cooled to 0° C. and 1 M LiOH (1.00 mL, 1.00 mmol) was added. The mixture was stirred for 20 h during which time the temperature reached rt after 1.5 h. The THF was removed in vacuo and the remaining aqueous solution was diluted with deionized H2O to a final volume of 3 mL. The aqueous mixture was extracted with Et2O (3×) and cooled to 0° C. 2 M HCl was added obtain pH=3. The mixture was extracted with EtOAc (3×) and the combined EtOAc portions were washed with brine, dried over MgSO4 and filtered through a Celite plug capped with a layer of MgSO4. The EtOAc solution was concentrated to give the title acid 8b as bronze foam scraped to beige solid; 62 mg, 83%, MS m/z 375.1 (ESI−, M−1).

Workup

  1. waitreached rt after 1.5 h
  2. customThe THF was removed in vacuo
  3. additionthe remaining aqueous solution was diluted with deionized H2O to a final volume of 3 mL
  4. extractionThe aqueous mixture was extracted with Et2O (3×)
  5. addition2 M HCl was added
  6. customobtain pH=3
  7. extractionThe mixture was extracted with EtOAc (3×)
  8. washthe combined EtOAc portions were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered through a Celite plug
  11. customcapped with a layer of MgSO4
  12. concentrationThe EtOAc solution was concentrated

Sources & evidence

ORD record
ord-6186b03ee9fc41069fd6bbbb5e5d446b
Source dataset
uspto-grants-2010_08
Patent number
US07781474B2

Reaction notes

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