Hydrochloric Acid → HCID 71525943, compound

HRID 1477798Notes

Reaction equation

HRID 1477798 reaction equation
C[O:2][C:3](=[O:26])[C@@H:4]([NH:9][C:10]([C:12]1[CH:17]=[N:16][C:15]([CH:18]2[CH2:20][CH2:19]2)=[C:14]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[N:13]=1)=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6].[OH-].[Li+].Cl>C1COCC1.O>[CH:18]1([C:15]2[N:16]=[CH:17][C:12]([C:10]([NH:9][C@@H:4]([C:5]([CH3:8])([CH3:7])[CH3:6])[C:3]([OH:26])=[O:2])=[O:11])=[N:13][C:14]=2[O:21][CH2:22][CH:23]2[CH2:24][CH2:25]2)[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71525400HCID 71525400, compound

Product 1

HCID 71525943HCID 71525943, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-[(5-cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carbonyl)-amino]-3,3-dimethyl-butyric acid methyl ester (58 mg, 160 μmol) in THF (3 mL) was added lithium hydroxide (30 mg, 715 μmol) in water (1 mL) and the mixture was stirred at reflux temperature for 3 hours. After cooling the mixture was poured into water (10 mL), acidified with 1 N HCl (1 mL) and extracted with TBME. Organic phases were combined, dried with Na2SO4, filtered and concentrated in vacuo to give the title compound (61 mg, quant.) as white solid; LC-MS (UV peak area/ESI) 100%, 348.1920 (M+H).

Workup

  1. temperatureat reflux temperature for 3 hours
  2. temperatureAfter cooling the mixture
  3. extractionextracted with TBME
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d4d57ca97ef4b38b2e84ec3c959ed15
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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