Hydrochloric Acid → HCID 68294084, compound

HRID 2279463Notes

Reaction equation

HRID 2279463 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:24])[CH2:9][C@H:10]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=1)[CH2:11][C:12]([O:14]C)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.O>[C:1]([O:5][C:6]([N:8]([CH3:24])[CH2:9][C@H:10]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=1)[CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68294584HCID 68294584, compound

Product 1

HCID 68294084HCID 68294084, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 102 (632 mg, 1.756 mmol) in 4:1 THF/H2O (5 mL) was added 3M aq. LiOH (5.855 mL, 17.56 mmol). The reaction mixture was stirred at RT for 4 h. The aqueous solution was acidified with 2N HCl to ca. pH 2-3 and then twice extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated to afford 598 mg (98.46%) of (S)-4-(tert-butoxycarbonyl(methyl)amino)-3-(4-chloro-3-fluorophenyl)butanoic acid (104).

Workup

  1. extractiontwice extracted with EtOAc
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e4329c434aca47989596994658c647fc
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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