Triethylamine → (N-benzyloxycarbonyl-N-methyl-O-benzyl-L-tyrosyl)-D-alanine methyl ester

HRID 484926Notes

Reaction equation

HRID 484926 reaction equation
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([N:19]([CH3:39])[C@H:20]([C:36]([OH:38])=O)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH3:47][O:48][C:49](=[O:53])[C@@H:50]([CH3:52])[NH2:51]>CC(C)=O.C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[CH3:47][O:48][C:49](=[O:53])[C@@H:50]([CH3:52])[NH:51][C:36](=[O:38])[C@H:20]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)[N:19]([C:17]([O:16][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:18])[CH3:39]

Participants

9

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 89020methyl D-alaninateHCID 13851003(S)-2-(((benzyloxy)carbonyl)(methyl)amino)-3-(4-(benzyloxy)phenyl)propanoic acid

Product 1

HCID 54187227(N-benzyloxycarbonyl-N-methyl-O-benzyl-L-tyrosyl)-D-alanine methyl esterYield 97%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of isobutyl chloroformate (2.00 g.) in acetone (10 ml.) was added dropwise to a solution of N-benzyloxycarbonyl-N-methyl-O-benzyl-L-tyrosine (6.0 g.) and triethylamine (1.45 g.) in acetone (60 ml.) with stirring and cooling to -10° C. A solution of D-alanine methyl ester (2.22 g.) and triethylamine (1.45 g.) in chloroform (30 ml.) was then added. Stirring was continued for one hour at -10° C., then overnight at room temperature. The mixture was stripped of solvents. Water and ethyl acetate were added to the residue. The ethyl acetate layer was washed with water, saturated aqueous sodium bicarbonate, water again, aqueous citric acid, water again and saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and stripped of ethyl acetate, affording (N-benzyloxycarbonyl-N-methyl-O-benzyl-L-tyrosyl)-D-alanine methyl ester (97% yield).

Workup

  1. stirringStirring
  2. customovernight
  3. customat room temperature
  4. washThe ethyl acetate layer was washed with water, saturated aqueous sodium bicarbonate, water again
  5. dry with materialaqueous citric acid, water again and saturated aqueous sodium chloride, dried over magnesium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-35aae1811c7f433b9beb3f748eaa220c
Source dataset
uspto-grants-1985_08
Patent number
US04533655

Reaction notes

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