Dichloromethane → H-Phe-Met-OMe.HCl

HRID 127604Notes

Reaction equation

HRID 127604 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:15][S:16][CH3:17])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)[Cl:30]>Cl>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:15][S:16][CH3:17])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:30]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 8022451tert-Butoxycarbonyl-phenylalanyl-methionine methyl ester

Product 1

HCID 67685067H-Phe-Met-OMe.HCl

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

11.83 g of Boc-Phe-Met-OMe (see Biochemistry, 8, 4183 (1969), incorporated herein) is dissolved in 100 ml methylene chloride after which HCl is passed into the solution for about 40 minutes. After evaporation of the solution to dryness, 75 ml ethyl acetate is added, resulting in a precipitate. The solid substance is separated by filtration, washed with petroleum ether, and dried. Melting point 123°-124° C. Rf in To:EtOH (8:2)=0.43 on SiO2.

Workup

  1. customAfter evaporation of the solution to dryness, 75 ml ethyl acetate
  2. additionis added
  3. customresulting in a precipitate
  4. customThe solid substance is separated by filtration
  5. washwashed with petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-6c4d992ebbd846aa81b24e6a96ca344f
Source dataset
uspto-grants-1981_03
Patent number
US04256736

Reaction notes

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