Z-Gln-ONp → H-Gln-Thr-Pro-OtBu

HRID 1680052Notes

Reaction equation

HRID 1680052 reaction equation
[NH2:1][C@H:2]([C:6]([N:8]1[CH2:19][CH2:18][CH2:17][C@H:9]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])[C@@H:3]([CH3:5])[OH:4].C1C=CC(COC([NH:30][C@H:31]([C:37](OC2C=CC([N+]([O-])=O)=CC=2)=[O:38])[CH2:32][CH2:33][C:34]([NH2:36])=[O:35])=O)=CC=1>CN(C=O)C>[NH2:30][C@H:31]([C:37]([NH:1][C@H:2]([C:6]([N:8]1[CH2:19][CH2:18][CH2:17][C@H:9]1[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[O:7])[C@@H:3]([CH3:5])[OH:4])=[O:38])[CH2:32][CH2:33][C:34](=[O:35])[NH2:36]

Participants

4

Reactant 2

HCID 111333Z-Gln-ONpHCID 131712118H-Thr-Pro-OtBu

Product 1

HCID 131712117H-Gln-Thr-Pro-OtBu

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.36 g H-Thr-Pro-OtBu is dissolved in 10 ml DMF, after which 1.93 g Z-Gln-ONp is added and the reaction mixture is stirred for about 20 hours at room temperature. After evaporation of the mixture to dryness, the residue is dissolved in EtOAc and washed consecutively with 5% KHSO4 solution, 5% NaHCO3 solution and a saturated NaCl solution. The solution is then dried over Na2SO4 and filtered, and the filtrate is evaporated to dryness.

Workup

  1. customAfter evaporation of the mixture to dryness
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed consecutively with 5% KHSO4 solution, 5% NaHCO3 solution
  4. dry with materialThe solution is then dried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-b22a67e408404ba19122d28e54dd56bc
Source dataset
uspto-grants-1981_06
Patent number
US04271152

Reaction notes

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