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

HRID 971560Notes

Reaction equation

HRID 971560 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-00f70023eef04ecdbccd5539f9c94744
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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