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

HRID 420111Notes

Reaction equation

HRID 420111 reaction equation
[CH2:1]([NH:8][C:9](=[O:34])[C@@H:10]([CH2:31][O:32][CH3:33])[NH:11]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>ClCCl>[CH2:1]([NH:8][C:9](=[O:34])[C@@H:10]([CH2:31][O:32][CH3:33])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54752467N-benzyl-O-methyl-N2-trityl-D-serinamide

Product 1

HCID 10104501(R)-2-Amino-N-benzyl-3-methoxypropionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 3 product (i.e. N-benzyl-O-methyl-N2-trityl-D-serinamide, 50 g) in dichloromethane (100 ml), hydrochloric acid (36%) was added at room temperature. This solution was stirred for 30 minutes at room temperature and then the solvent was completely recovered under vacuum at 40° C. Water (250 ml) was added to it at room temperature and the aqueous layer was neutralized with aqueous ammonia (20 ml). The aqueous layer was extracted with toluene (2×200 ml). The toluene was then completely recovered under vacuum at 50-55° C. to get an oil. Yield=15 gm.

Workup

  1. customthe solvent was completely recovered under vacuum at 40° C
  2. additionWater (250 ml) was added to it at room temperature
  3. extractionThe aqueous layer was extracted with toluene (2×200 ml)
  4. customThe toluene was then completely recovered under vacuum at 50-55° C.
  5. customto get an oil

Sources & evidence

ORD record
ord-861d5d6e16534e31accd918b19bace6f
Source dataset
uspto-grants-2012_01
Patent number
US08093426B2

Reaction notes

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