Allyl 2,2,2-Trichloroacetimidate → HCID 13995645, compound

HRID 1682433Notes

Reaction equation

HRID 1682433 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][OH:17])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].ClC(Cl)(Cl)C(=N)O[CH2:23][CH:24]=[CH2:25]>C(Cl)Cl.C1CCCCC1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][O:17][CH2:25][CH:24]=[CH2:23])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 2

HCID 316905Allyl 2,2,2-TrichloroacetimidateHCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

Product 1

HCID 13995645HCID 13995645, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

Dissolve N-(benzyloxycarbonyl)-L-serine methyl ester (63 mmol) in methylene chloride/cyclohexane (1:1, 600 mL). Add allyl trichloroacetimidate (26 g, 128 mmol) and trifluroromethanesulfonic acid (5 mL, 56.6 mmol). Stir at room temperature under a nitrogen atmosphere for 5 hours and dilute with methylene chloride. Wash with saturated aqueous sodium hydrogen carbonate, water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give N-(benzyloxycarbonyl)-O-2-propenyl-L-serine methyl ester.

Workup

  1. washWash with saturated aqueous sodium hydrogen carbonate, water
  2. dry with materialdry (MgSO4)
  3. customevaporate the solvent in vacuo
  4. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-68d19dc374a24a92a449feea2e3b0a90
Source dataset
uspto-grants-1997_06
Patent number
US05635502

Reaction notes

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