Triethylamine → HCID 178501424, compound

HRID 620061

Reaction equation

HRID 620061 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:22][O:23][C:24](=[O:33])[C@H:25]([CH2:27][C:28]1[N:32]=[CH:31][NH:30][CH:29]=1)[NH2:26].C(N(CC)CC)C.CC(C)=O.C(=O)=O>C(Cl)Cl.C(OCC)(=O)C>[CH3:22][O:23][C:24](=[O:33])[C@H:25]([CH2:27][C:28]1[N:32]=[CH:31][NH:30][CH:29]=1)[NH:26][C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 18522661Acetone cardiceHCID 178419105HCID 178419105, compound

Product 1

HCID 178501424HCID 178501424, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

43.73 g (164 mmol) of N-tert.-butoxycarbonyl-L-phenylalanine and 34.5 g (142 mmol) of L-histidine methyl ester dihydrochloride are taken in 400 ml of methylene chloride. 100 g (1 mol) of triethylamine are added at -20° C. (acetone/dry ice bath), while stirring. 111 ml (0.171 mol) of propanephosphonic acid anhydride solution (50% strength in methylene chloride) are now added dropwise to the cooled mixture. The mixture is allowed to warm to room temperature overnight. The solvent is stripped off and the crude product is taken up in 500 ml of ethyl acetate. The organic phase is washed 4 times with 200 ml of saturated sodium bicarbonate solution each time, 3 times with 0.1N hydrochloric acid and once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo.

Workup

  1. washThe organic phase is washed 4 times with 200 ml of saturated sodium bicarbonate solution each time, 3 times with 0.1N hydrochloric acid
  2. dry with materialonce with saturated sodium chloride solution, dried over magnesium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-424864dd986c4fbc8974bbe9e2738ba8
Source dataset
uspto-grants-1989_04
Patent number
US04818748

Linked notes

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