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

HRID 389384Notes

Reaction equation

HRID 389384 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° C. to 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° C. to 55° C.
  5. customto get an oil

Sources & evidence

ORD record
ord-de275a8ffb0c4868a8a238ec4893da7b
Source dataset
uspto-grants-2013_02
Patent number
US08378142B2

Reaction notes

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