Hydrochloric Acid → Benzyloxycarbonylglycyl-glycyl-serine hydrazide

HRID 986352Notes

Reaction equation

HRID 986352 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:21]1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.C[O:44][C:45](=O)[C@H:46](CO)[NH2:47].Cl.C(N1CCCCC1)C.C[N:61](C)[CH:62]=[O:63]>>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH:15][CH2:16][C:17]([NH:47][C@H:46]([C:62]([NH:61][NH2:21])=[O:63])[CH2:45][OH:44])=[O:19])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 13007N-EthylpiperidineHCID 80170N-HydroxysuccinimideHCID 95686CarbobenzoxyglycylglycineHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoate

Product 1

HCID 14369437Benzyloxycarbonylglycyl-glycyl-serine hydrazide

Conditions

Temperature
-10 °C

Procedure

A solution of benzyloxycarbonylglycyl-glycine (13.31 g, 50 mmoles), N-hydroxysuccinimide (5.75 g) and N, N'-dicyclohexylcarbodiimide (11.3 g) in dimethylformamide (180 ml) is stirred and cooled (-10° C.) for 1 hour. A precooled (-10° C.) solution of serine methyl ester, liberated from its hydrochloride (7.8 g, 50 mmoles) with N-ethylpiperidine (6.85 ml), in the same solvent (50 ml) is added, and the reaction mixture is stirred for 3 hours at 0° C. and allowed to stand for 8 hours at room temperature; the N, N'-dicyclohexylurea precipitate is filtered off and the filtrate is admixed with 100% hydrazine hydrate (15 ml). After 3 days of standing at room temperature, the formed hydrazide is separated, washed with ethanol and crystallized from aqueous ethanol. Yield 15.2 g (83%), m.p. 172-175 (unchanged after recrystallization). Composition: C15H21N5O6.

Workup

  1. additionis added
  2. waitto stand for 8 hours at room temperature
  3. filtrationthe N, N'-dicyclohexylurea precipitate is filtered off
  4. waitAfter 3 days of standing at room temperature
  5. customthe formed hydrazide is separated
  6. washwashed with ethanol
  7. customcrystallized from aqueous ethanol
  8. customYield 15.2 g (83%), m.p. 172-175 (unchanged after recrystallization)

Sources & evidence

ORD record
ord-7fd41a3510ee4691a0c28e0daa218e4e
Source dataset
uspto-grants-1987_12
Patent number
US04711952

Reaction notes

Loading…