Chloroform → HCID 178501425, compound

HRID 1733662Notes

Reaction equation

HRID 1733662 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH2:7].C(Cl)(Cl)Cl.[CH2:19]([O:26][C:27]([NH:29][C@H:30]([C:36](O)=[O:37])[CH2:31][CH2:32][C:33](=[O:35])[NH2:34])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CS(ON1C2C=CC=CC=2N=N1)(=O)=O>C(N(CC)CC)C>[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH:7][C:36](=[O:37])[C@H:30]([CH2:31][CH2:32][C:33](=[O:35])[NH2:34])[NH:29][C:27]([O:26][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:28]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 75855L-Glutamine, N2-[(phenylmethoxy)carbonyl]-HCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl esterHCID 178419105HCID 178419105, compound

Product 1

HCID 178501425HCID 178501425, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

L-Histidine methyl ester dihydrochloride (1.21 g) is suspended into chloroform (20 ml), and therto are added triethylamine (1.40 ml) and further N-benzyloxycarbonyl-L-glutamine (1.40 g) and triethylamine (0.70 ml). After stirring for a while, to the mixture is added 1-methanesulfonyloxy-1,2,3-benzotriazole (1.07 g) and the mixture is stirred for 1 hour. After allowing to stand overnight, the solvent is distilled off. To the residue are added water and 1 N aqueous sodium hydrogen carbonate and the mixture is cooled. The precipitated gelling product is separated by filtration and washed with water. The product is heated together with a small amount of water and cooled. The precipitated by filtration to give N-(N-benzyloxycarbonyl-L-glutaminyl)-L-histidine methyl ester (1.25 g), melting point: 186°-188° C.

Workup

  1. stirringthe mixture is stirred for 1 hour
  2. distillationthe solvent is distilled off
  3. additionTo the residue are added water and 1 N aqueous sodium hydrogen carbonate
  4. temperaturethe mixture is cooled
  5. customis separated by filtration
  6. washwashed with water
  7. temperatureThe product is heated together with a small amount of water
  8. temperaturecooled
  9. customThe precipitated by filtration

Sources & evidence

ORD record
ord-403788dde4b8450f81cbc789ca2ac1ea
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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