Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | L-Glutamine, N2-[(phenylmethoxy)carbonyl]- | HCID 75855 | — |
| Reactant | Methanesulfonic acid, 1H-benzotriazol-1-yl ester | HCID 11745953 | — |
| Reactant | HCID 178419105 | HCID 178419105 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 178501425 | HCID 178501425 | 58% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04242507 |
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| Source dataset | uspto-grants-1980_12 |
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| ORD ID | ord-403788dde4b8450f81cbc789ca2ac1ea |
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| Source note | uspto-grants-1980_12 |
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