Lithium hydroxide, monohydrate → (S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acid

HRID 1365019Notes

Reaction equation

HRID 1365019 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]([NH:9][C:10]([O:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6].O.[OH-].[Li+]>C1COCC1.CO.O>[C:13]12([O:12][C:10]([NH:9][C@@H:4]([C:5]([CH3:8])([CH3:7])[CH3:6])[C:3]([OH:23])=[O:2])=[O:11])[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:21]3)[CH2:20]1)[CH2:22]2

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57945074(S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acid methyl ester

Product 1

HCID 57945076(S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acidYield 85.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acid methyl ester (358 mg, 1.107 mmol) in THF (4 mL) and MeOH (4 mL) was added a pre-made solution of lithium hydroxide monohydrate (93 mg, 2.214 mmol) in water (4.00 mL). The cloudy white solution was stirred at rt for 5 hrs. The volatiles were removed, and the reaction mixture was diluted with dilute citric acid solution and extracted with EtOAc (3×10 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated to obtain a white solid (291.4 mg, 85%) as product. The crude material was used without further purification.

Workup

  1. customThe volatiles were removed
  2. additionthe reaction mixture was diluted with dilute citric acid solution
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-94e81e0b987347149f1a75a9967b934c
Source dataset
uspto-grants-2011_02
Patent number
US07888464B2

Reaction notes

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