2-Phenylglycine → HCID 3509812, compound

HRID 892628Notes

Reaction equation

HRID 892628 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:19][C:20]([F:27])([F:26])[C:21](OCC)=[O:22]>CO>[C:4]1([CH:7]([C:8]([OH:10])=[O:9])[NH:11][C:21](=[O:22])[C:20]([F:27])([F:26])[F:19])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 38662-PhenylglycineHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 3509812HCID 3509812, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of DL-phenylglycine (15.1 g, 0.10 mol) in methanol is treated with triethylamine (10.1 g, 0.10 mol) and ethyl trifluoroacetate (17.8 g, 0.125 mol), stirred at room temperature for 72 hours, diluted with methanol and treated with Dowex 50× acidic resin. The reaction mixture is stirred for 10 minutes and filtered. The filtrate is concentrated in vacuo to give a pale yellow solid which is recrystallized from 1,2-dichloroethane to give the title product as white needles, 10.5 g (42% yield), mp 155-157° C.

Workup

  1. additiontreated with Dowex 50× acidic resin
  2. stirringThe reaction mixture is stirred for 10 minutes
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto give a pale yellow solid which
  6. customis recrystallized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-741c1220872e4acc817022b4c27b1b47
Source dataset
uspto-grants-1992_06
Patent number
US05118816

Reaction notes

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