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

HRID 420112Notes

Reaction equation

HRID 420112 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.C(O)(=O)C>C(O)C>[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 176Acetic 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 702EthanolSolvent

Procedure

To a solution of Example 3 product (i.e., N-benzyl-O-methyl-N2-trityl-D-serinamide, 50 g) in absolute ethanol (100 ml), acetic acid (1.25 mole eq.) 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=18 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-07b9c5f799254f8290de33dbfe07138c
Source dataset
uspto-grants-2012_01
Patent number
US08093426B2

Reaction notes

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