Hydrochloric Acid → HCID 66954873, compound

HRID 2190966Notes

Reaction equation

HRID 2190966 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][C:14]([F:20])([F:19])[CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.[ClH:21]>C(#N)C>[ClH:21].[NH2:8][C@@H:9]([CH2:13][C:14]([F:19])([F:20])[CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53348251HCID 53348251, compound

Product 1

HCID 66954873HCID 66954873, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(5)-2-(tert-butoxycarbonylamino)-5-cyclopropyl-4,4-difluoropentanoic acid (75 g, 0.256 mol, 1 eq), prepared as in Example 10, was added to a 2 L round bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer. A mixture of hydrochloric acid (13.7 g, 0.375 mol, 1.5 eq) and acetonitrile (750 mL) and was added. White solids precipitated out during the reaction. After 2 hours the solids were filtered, washed with acetonitrile and dried in a vacuum oven at 30° C. for 24 hours to provide (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid hydrochloride (51 g, 87% yield). 1H NMR confirmed the desired structure.

Workup

  1. additionwas added to a 2 L round bottomed flask
  2. customfitted with a mechanical stirrer, nitrogen inlet
  3. additionwas added
  4. customWhite solids precipitated out during the reaction
  5. filtrationAfter 2 hours the solids were filtered
  6. washwashed with acetonitrile
  7. customdried in a vacuum oven at 30° C. for 24 hours

Sources & evidence

ORD record
ord-4b03da25f65c49feba0723f37d0c5a56
Source dataset
uspto-grants-2012_12
Patent number
US08324417B2

Reaction notes

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