Z-Thr(tBu)-OSU → Z-Thr(tBu)-Ala-Ile-Gly-OMe

HRID 1580886Notes

Reaction equation

HRID 1580886 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:12]([NH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:13])[C@H:8]([CH2:10][CH3:11])[CH3:9])=[O:5])[CH3:3].[CH3:20][C@@H:21]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[C@H:22]([NH:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[C:23](ON1C(=O)CCC1=O)=[O:24]>CN(C)C=O>[NH:33]([C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[C@H:22]([C:23]([NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C:12]([NH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:13])[C@H:8]([CH2:10][CH3:11])[CH3:9])=[O:5])[CH3:3])=[O:24])[C@@H:21]([CH3:20])[O:44][C:45]([CH3:47])([CH3:48])[CH3:46]

Participants

4

Reactant 2

HCID 13503275Z-Thr(tBu)-OSUHCID 131709978H-Ala-Ile-Gly-OMe

Product 1

HCID 131709985Z-Thr(tBu)-Ala-Ile-Gly-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.36 g of H-Ala-Ile-Gly-OMe (compare Example 1) and 2.5 g of Z-Thr(tBu)-OSU in 3 ml of dimethylformamide are stirred for 20 hours at room temperature. The tetrapeptide derivative is precipitated by ether, filtered off and washed with ether. After recrystallisation from ethanol the melting point is 229°-230°C. [α]D20 = -43° (c = 1 in methanol). Rf = 0.55 in the system chloroform-methanol (95:5) on silica gel.

Workup

  1. customThe tetrapeptide derivative is precipitated by ether
  2. filtrationfiltered off
  3. washwashed with ether
  4. customAfter recrystallisation from ethanol the melting point is 229°-230°C. [α]D20 = -43° (c = 1 in methanol)

Sources & evidence

ORD record
ord-edd5bb15b53b407583e7db27ee78ef5d
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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