Dimethylformamide → HCID 14999135, compound

HRID 569687Notes

Reaction equation

HRID 569687 reaction equation
[C:1]([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O[N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34].CN(C)C=O.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:5]1([CH2:4][O:3][C:1]([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([O:26][N:28]2[C:32](=[O:33])[CH2:31][CH2:30][C:29]2=[O:34])=[O:25])[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:14])=[O:2])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 6998938Z-Gly-phe-OH

Product 1

HCID 14999135HCID 14999135, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A 7.17 g portion of carbobenzyloxy glycyl-L-phenylalanine and 2.30 g of N-hydroxysuccinimide were slurried in 100 ml of acetonitrile, cooled in an ice bath, with the addition of 5 ml of dimethylformamide, to obtain solution. A precooled solution of 4.12 g of dicyclohexylcarbodiimide in 50 ml of acetonitrile was added dropwise. The mixture was stirred in the ice bath for 2 hours, then refrigerated overnight, filtered and the filtrate concentrated in vacuo. The residue was taken up in 125 ml of ethyl acetate, washed with precooled 5% aqueous sodium bicarbonate, then twice with water, dried and concentrated in vacuo. The residue was dissolved in 125 ml of 2-propanol and refrigerated overnight. The resulting gum was taken up in tetrahydrofuran and concentrated in vacuo, giving 6.5 g of 1-[[N-[N-[(phenylmethoxy)carbonyl]glycyl]-L-phenylalanyl]oxy]-2,5-pyrrolidinedione.

Workup

  1. customto obtain solution
  2. filtrationrefrigerated overnight, filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. washwashed with precooled 5% aqueous sodium bicarbonate
  5. dry with materialtwice with water, dried
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in 125 ml of 2-propanol and refrigerated overnight
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e224c9a82e145bb91f5aef4731d36c1
Source dataset
uspto-grants-1988_03
Patent number
US04732970

Reaction notes

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