Hydrochloric Acid → (R)-2-Amino-N-benzyl-3-methoxypropionamide

HRID 2093020Notes

Reaction equation

HRID 2093020 reaction equation
[CH2:1]([NH:8][C:9](=[O:22])[C@H:10]([NH:14]C(=O)OC(C)(C)C)[CH2:11][O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH-])C1C=CC=CC=1.Cl>ClCCl>[NH2:14][C@H:10]([CH2:11][O:12][CH3:13])[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22619318Benzyl amideHCID 46223141tert-Butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate

Product 1

HCID 10104501(R)-2-Amino-N-benzyl-3-methoxypropionamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution (5° C.) of 3.36 g of Intermediate 5, benzylamide in 40 mL of dichloromethane was added 6.02 mL of 36% HCl. The reaction mixture was stirred at room temperature until no starting material was observed by TLC. The organic phase was washed with 1N HCl (2×30 mL) and the combined aqueous phase basified to 10-12 with 25% NaOH. After saturating the aqueous phase with sodium chloride, it was extracted with dichloromethane (3×30 mL). The organic phase was dried and concentrated under vacuum yielding 2.01 g of a pale yellow oil.

Workup

  1. washThe organic phase was washed with 1N HCl (2×30 mL)
  2. concentrationAfter saturating the aqueous phase with sodium chloride, it
  3. extractionwas extracted with dichloromethane (3×30 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-efdb51c2495e471682ec31837d765363
Source dataset
uspto-grants-2013_05
Patent number
US08440861B2

Reaction notes

Loading…