Hydrochloric Acid → (S)-2-Amino-3-cyclopropyl-N,N-dimethylpropanamide hydrochloride

HRID 632276Notes

Reaction equation

HRID 632276 reaction equation
[ClH:1].O1CCOCC1.[CH:8]1([CH2:11][C@H:12]([NH:18]C(=O)OC(C)(C)C)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:10][CH2:9]1>C(O)C>[ClH:1].[NH2:18][C@@H:12]([CH2:11][CH:8]1[CH2:10][CH2:9]1)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68085200HCID 68085200, compound

Product 1

HCID 86674779(S)-2-Amino-3-cyclopropyl-N,N-dimethylpropanamide hydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 4M solution of HCl in dioxane (4.68 mL, 18.7 mmol) was added to a solution of (S)-tert-butyl 3-cyclopropyl-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (1.2 g, 4.68 mmol) in ethanol (10 mL). After 16 h stirring at ambient temperature the solvent was removed under reduced pressure. The remaining solid was digerated with diethyl ether (10 mL), filtered off, washed with diethyl ether (3×5 mL) and dried for 3 h in vacuo at 40° C. to give the title compound as off-white solid (820 mg, 91%). MS (EI): m/e=157.1 [M+H]+.

Workup

  1. customwas removed under reduced pressure
  2. filtrationfiltered off
  3. washwashed with diethyl ether (3×5 mL)
  4. customdried for 3 h in vacuo at 40° C.

Sources & evidence

ORD record
ord-b8b279ec6630455ba0480d2e2a96e067
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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