Azide → HCID 13071899, compound

HRID 1995271Notes

Reaction equation

HRID 1995271 reaction equation
[NH2:1][C@H:2]([C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][C:10](=[O:12])[NH2:11])=[O:6])[CH2:3][OH:4].[N-]=[N+]=[N-]>>[NH2:1][CH2:2][C:5]([NH:7][CH2:8][C:13]([NH:1][C@H:2]([C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][C:10](=[O:12])[NH2:11])=[O:6])[CH2:3][OH:4])=[O:14])=[O:6]

Participants

3

Reactant 2

HCID 33558AzideHCID 7016076L-Asparagine, L-seryl-

Product 1

HCID 13071899HCID 13071899, compoundYield 63%

Procedure

H-Ser-Asn-OH prepared in (1) and benzyloxycarbonyl-Gly-Gly-NHNH2 were condensed according to the azide method, and the reaction mixture was extracted with n-butanol to separate benzyloxycarbonyl-Gly-Gly-Ser-Asn-OH as a product. The product was subjected to catalytic hydrogenating decomposition in the presence of 5% palladium on carbon to obtain H-Gly-Gly-Ser-Asn-OH melting at 219° C. with decomposition in a yield of 63%.

Workup

  1. customcondensed
  2. extractionthe reaction mixture was extracted with n-butanol
  3. customto separate benzyloxycarbonyl-Gly-Gly-Ser-Asn-OH as a product

Sources & evidence

ORD record
ord-c5aacbe5832e4f759ae7fe806f50468e
Source dataset
uspto-grants-1983_09
Patent number
US04404133

Reaction notes

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