Hydrochloric Acid → Z-Gln-Asn-Phe-OCH3

HRID 971564Notes

Reaction equation

HRID 971564 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:18]([O:20]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:13][CH2:14][C:15]([NH2:17])=[O:16])=[O:10])=[CH:3][CH:2]=1.[NH2:30][C@H:31]([C:36]([NH:38][C@H:39]([C:47]([O:49][CH3:50])=[O:48])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:37])[CH2:32][C:33](=[O:35])[NH2:34].Cl>CN(C)C=O.C(N(CC)CC)C>[NH:11]([C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:10])[C@H:12]([C:18]([NH:30][C@H:31]([C:36]([NH:38][C@H:39]([C:47]([O:49][CH3:50])=[O:48])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:37])[CH2:32][C:33](=[O:35])[NH2:34])=[O:20])[CH2:13][CH2:14][C:15](=[O:16])[NH2:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 111333Z-Gln-ONpHCID 15567215Asparaginyl-phenylalanine methyl ester

Product 1

HCID 131709988Z-Gln-Asn-Phe-OCH3

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

14.5 g of Z-Gln-ONP and 10.8 g of H-Asn-Phe-OCH3, hydrochloride (Ann. 688, 259 [ 1965]) are dissolved together in 100 ml of dimethylformamide and to the solution 4.55 ml of triethylamine are added slowly. A thick paste forms which is diluted with 50 of dimethylformamide. After a reaction period of 24 hours at room temperature, the batch is filtered and the residue washed with dimethylformamide. The resulting Z-Gln-Asn-Phe-OMe can be recrystallized from much hot dimethylformamide. Melting point, 261°-265° C. (decomp.). [α]D20 = + 11° (c = 0.94 in hexamethylphosphoric acid triamide).

Workup

  1. additionare added slowly
  2. customAfter a reaction period of 24 hours at room temperature
  3. filtrationthe batch is filtered
  4. washthe residue washed with dimethylformamide
  5. customThe resulting Z-Gln-Asn-Phe-OMe can be recrystallized from much hot dimethylformamide
  6. custom[α]D20 = + 11° (c = 0.94 in hexamethylphosphoric acid triamide)

Sources & evidence

ORD record
ord-8834683e5b8b412bb7c912d61a1714dd
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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