Triethylamine → Z-Thr(tBu)-Phe-Pro-OH

HRID 1580885Notes

Reaction equation

HRID 1580885 reaction equation
[CH3:1][C@@H:2]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:3]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:4]([O:6]N1C(=O)CCC1=O)=O.[NH2:30][C@H:31]([C:39]([N:41]1[CH2:48][CH2:47][CH2:46][C@H:42]1[C:43]([OH:45])=[O:44])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C>CN(C)C=O>[NH:14]([C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[C@H:3]([C:4]([NH:30][C@H:31]([C:39]([N:41]1[CH2:48][CH2:47][CH2:46][C@H:42]1[C:43]([OH:45])=[O:44])=[O:40])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:6])[C@@H:2]([CH3:1])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7020642Phe-ProHCID 13503275Z-Thr(tBu)-OSU

Product 1

HCID 131709981Z-Thr(tBu)-Phe-Pro-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20.2 g of Z-Thr(tBu)-OSU, 13.3 g of H-Phe-Pro-OH (monohydrate) and 6.54 ml of triethylamine are dissolved in 80 ml of dimethylformamide, allowed to stand overnight at about 20°C and then concentrated in a high vacuum until a sticky mass forms. The latter is dissolved in 500 ml of ethyl acetate and washed five times with 100 ml at a time of 5 % strength tartaric acid solution and subsequently with water until neutral. The organic phase is concentrated to dryness and the remaining solid foam is powdered and dried in a high vacuum at 40°C. On twice reprecipitating from ethyl acetate-peptroleum ether 13.3 g of amorphous chromatographically pure tripeptide derivative having an unsharp melting range at about 75°-85°C are obtained. In a thin layer chromatogram on silica gel RF115 = 0.68; Rf121A = 0.57.

Workup

  1. concentrationconcentrated in a high vacuum until a sticky mass forms
  2. dissolutionThe latter is dissolved in 500 ml of ethyl acetate
  3. washwashed five times with 100 ml at a time of 5 % strength tartaric acid solution
  4. concentrationThe organic phase is concentrated to dryness
  5. customdried in a high vacuum at 40°C
  6. customOn twice reprecipitating from ethyl acetate-peptroleum ether 13.3 g of amorphous chromatographically pure tripeptide derivative
  7. customat about 75°-85°C
  8. customare obtained

Sources & evidence

ORD record
ord-6a41c8bb9be947c180f15f608c1b603d
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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