4-Methylmorpholine → Trt-Gly-Gly-Phe-Gly-OBz

HRID 989574

Reaction equation

HRID 989574 reaction equation
[NH:1]([C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][C:3]([NH:5][CH2:6][C:7](O)=[O:8])=[O:4].[OH:29]N1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:52][C@H:53]([C:61]([NH:63][CH2:64][C:65]([O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:66])=[O:62])[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.CN1CCOCC1>CN(C=O)C>[NH:1]([C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:52][C@H:53]([C:61]([NH:63][CH2:64][C:65]([O:67][C:68]([C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)=[O:29])=[O:66])=[O:62])[CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)=[O:8])=[O:4]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 14217166N-(Triphenylmethyl)glycylglycineHCID 91977316Phe-Gly-OBzl

Product 1

HCID 131723527Trt-Gly-Gly-Phe-Gly-OBz

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 10 ml of dry DMF were added 1.54 g of Trt-Gly-Gly, 0.52 g of N-hydroxysuccinimide and 0.93 g of DCC, followed by effecting a reaction at 4° C. for 3 hours, to thereby obtain a reaction mixture. To the obtained reaction mixture was added a DMF solution containing 2.0 g of Phe-Gly-OBn para-toluenesulfonate synthesized in item (1) and 0.41 g of N-methylmorpholine, which are dissolved in 10 ml of DMF, followed by effecting a reaction at 4° C. for 15 hours, to thereby obtain a reaction mixture. A precipitate contained in the obtained reaction mixture was removed and the resultant solution was evaporated to dryness, to thereby obtain a residue. The obtained residue was purified by silica gel column chromatography (silica gel: Art No. 9365, Silica gel 60, 200-400 mesh, manufactured and sold by E. Merck, Darmstadt, Germany, eluent: chloroform/methanol=20/1), to thereby obtain 1.5 g of Trt-Gly-Gly-Phe-Gly-OBz.

Workup

  1. customa reaction at 4° C. for 3 hours
  2. customto thereby obtain a reaction mixture
  3. customTo the obtained reaction mixture
  4. customa reaction at 4° C. for 15 hours
  5. customto thereby obtain a reaction mixture
  6. customA precipitate contained in the obtained reaction mixture
  7. customwas removed
  8. customthe resultant solution was evaporated to dryness
  9. customto thereby obtain a residue
  10. customThe obtained residue was purified by silica gel column chromatography (silica gel: Art No. 9365, Silica gel 60, 200-400 mesh, manufactured and sold by E. Merck, Darmstadt, Germany, eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-ad867d2c90d8478fa63c44df7dbe56a8
Source dataset
uspto-grants-2002_10
Patent number
US06458347B1

Linked notes

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