4-Methylmorpholine → (S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

HRID 1030521Notes

Reaction equation

HRID 1030521 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:24]1CCOCC1.C(OC(Cl)=O)C(C)C>O1CCCC1>[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:20]([NH2:24])=[O:22])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 70878Benzyloxycarbonyl-L-phenylalanine

Product 1

HCID 2755911(S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An 18 g portion of Nα -[(phenylmethoxy)carbonyl]-L-phenylalanine and 6.6 ml of N-methylmorpholine were dissolved in 150 ml of tetrahydrofuran and stirred at 31 10° C. as 8.04 ml of isobutylchloroformate was added. After 1 minute, ammonia gas was bubbled through the mixture until it was saturated. The mixture was stirred an additional 30 minutes and then poured into ice-water. The white solid was collected, giving 16.76 g of the desired compound, mp 164°-165° C.

Workup

  1. additionwas added
  2. customammonia gas was bubbled through the mixture until it
  3. additionpoured into ice-water
  4. customThe white solid was collected

Sources & evidence

ORD record
ord-fd25ff99e6cb4c3ca3fa63d793148cd7
Source dataset
uspto-grants-1992_04
Patent number
US05106835

Reaction notes

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