Chloroform → HCID 11508813, compound

HRID 971851Notes

Reaction equation

HRID 971851 reaction equation
[NH2:1][C@H:2]([C:10]([O:12][CH3:13])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.C(Cl)(Cl)[Cl:16]>C(Cl)Cl>[NH2:1][C@H:2]([C:10]([NH:1][C@H:2]([C:10]([O:12][CH3:13])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[ClH:16]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 11508813HCID 11508813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The C-terminal tetrapeptide (ε-INOC)Lys-Asn-Phe-Phe-OMe.2HCl is prepared by reacting Phe-OMe hydrochloride with BOC-PheHSE, which reaction is conducted in a suitable organic solvent, such as chloroform or methylene chloride, overnight at a basic pH. Insoluble materials are separated and the organic solution evaporated to dryness and the residue recrystallized. The blocked dipeptide is treated with anhydrous hydrogen chloride in ethyl acetate, thereby cleaving the BOC substituent to form Phe-Phe-OMe hydrochloride.

Workup

  1. customwith BOC-PheHSE, which reaction
  2. customInsoluble materials are separated
  3. customthe organic solution evaporated to dryness
  4. customthe residue recrystallized
  5. additionThe blocked dipeptide is treated with anhydrous hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-4943b2f2eee344f69d46a4f0933e1ccf
Source dataset
uspto-grants-1979_07
Patent number
US04161521

Reaction notes

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