Triethylamine → Z-Gln-Asp(OtBu)-Phe-OCH3

HRID 971542Notes

Reaction equation

HRID 971542 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:22]([O:24][CH3:25])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].Cl.[CH:27]1[CH:32]=[CH:31][C:30]([CH2:33][O:34][C:35]([NH:37][C@H:38]([C:44](OC2C=CC([N+]([O-])=O)=CC=2)=[O:45])[CH2:39][CH2:40][C:41]([NH2:43])=[O:42])=[O:36])=[CH:29][CH:28]=1.C(N(CC)CC)C>CN(C)C=O>[NH:37]([C:35]([O:34][CH2:33][C:30]1[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=1)=[O:36])[C@H:38]([C:44]([NH:1][C@H:2]([C:11]([NH:13][C@H:14]([C:22]([O:24][CH3:25])=[O:23])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:45])[CH2:39][CH2:40][C:41](=[O:42])[NH2:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111333Z-Gln-ONpHCID 131711563H-Asp(OtBu)-Phe-OCH3.HCl

Product 1

HCID 131711562Z-Gln-Asp(OtBu)-Phe-OCH3

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

550 mg of H-Asp(OtBu)-Phe-OCH3.HCl together with 574 mg of Z-Gln-ONP are dissolved in 2.5 ml of absolute N,N-dimethylformamide and stirred with 0.20 ml of triethylamine for 15 hours at 30°-33° C. bath temperature. Thereafter the product is extracted by shaking with a large amount of ethyl acetate as described under 19 and the solution is dried and evaporated.

Workup

  1. extractionThereafter the product is extracted
  2. customthe solution is dried
  3. customevaporated

Sources & evidence

ORD record
ord-f017a377cb684d529119602f821e0abc
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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