Benzylamine → (R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

HRID 1401870Notes

Reaction equation

HRID 1401870 reaction equation
CN1CCOCC1.C(OC(Cl)=O)C(C)C.[C:16]([NH:19][C@H:20]([CH2:24][OH:25])[C:21]([OH:23])=O)(=[O:18])[CH3:17].[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[C:16]([NH:19][C@H:20]([CH2:24][OH:25])[C:21]([NH:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 10844522N-Acetyl-D-serine

Product 1

HCID 10889901(R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
32.5 °C

Procedure

4-methylmorpholine (7.3 ml) followed by isobutylchloroformate (12.35 ml) was added to a suspension of (R)-2-acetamido-3-hydroxypropanoic acid (7 grams) in tetrahydrofuran (147 ml) at −78 to −75° C., benzylamine (10.4 ml) was added to it and the reaction mixture temperature was raised to 30-35° C. then stirred for 30 minutes. The reaction mixture was filtered and the filtrate was distilled off under reduced pressure. The obtained residue was dissolved in methylene chloride (35 ml) and washed with aqueous hydrochloric acid followed by sodium carbonate and then with water. The solvent from the methylene chloride layer was distilled off completely under reduced pressure to get the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe filtrate was distilled off under reduced pressure
  3. dissolutionThe obtained residue was dissolved in methylene chloride (35 ml)
  4. washwashed with aqueous hydrochloric acid
  5. distillationThe solvent from the methylene chloride layer was distilled off completely under reduced pressure

Sources & evidence

ORD record
ord-9c2ebfb40b954fc9b72c201de48a8ff3
Source dataset
uspto-grants-2014_12
Patent number
US08907132B2

Reaction notes

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