L-Phenylalanine → phenylalanine O-benzyl ester

HRID 883540Notes

Reaction equation

HRID 883540 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(NC(=NC(C)C)O[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(C)C>O1CCCC1>[NH2:1][CH:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([O:12][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:11]

Participants

4

Reactant 2

HCID 6140L-PhenylalanineHCID 11128254o-Benzyl-n,n'-diisopropylisourea

Product 1

HCID 102533phenylalanine O-benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a dry round bottomed flask, equipped with a magnetic stirrer, 13.22 g (80 mmol) of Phenylalanine is added to 18.75 g (80 mmol) of the oil, N,N′-diisopropyl-O-benzylisourea and stirred at room temperature for about one hour. After about one hour the volume of the reaction is increased by the addition of 350 mL of dry tetrahyrdofuran (THF), and stirred at room temperature for an additional 48 hours. The resultant mixture is then filtered in order to remove the by-product, diisopropylurea, and the THF is then evaporated from the filtrate at reduced pressure. The oil which remains is pumped under high vacuum for about 24 hours yielding the protected amino acid, benzyl 2-amino-3-phenylpropanoate, in pure enough form for subsequent steps.

Workup

  1. customIn a dry round bottomed flask, equipped with a magnetic stirrer
  2. stirringstirred at room temperature for an additional 48 hours
  3. filtrationThe resultant mixture is then filtered in order
  4. customto remove the by-product, diisopropylurea
  5. customthe THF is then evaporated from the filtrate at reduced pressure
  6. waitThe oil which remains is pumped under high vacuum for about 24 hours

Sources & evidence

ORD record
ord-cd1f7da961a54de6bc42f003e8aa647c
Source dataset
uspto-grants-2012_08
Patent number
US08236952B2

Reaction notes

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