Water → HCID 53692132, compound

HRID 1078619Notes

Reaction equation

HRID 1078619 reaction equation
C(O)(=O)C(O)=O.C([O:11][C:12](=[O:26])[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:15]1=[O:25])(C)(C)C.[CH2:27]([O:34][C:35]([NH:37][C@H:38]([C:50](O)=[O:51])[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:27]([O:34][C:35]([NH:37][C@H:38]([C:50]([N:17]1[CH2:18][CH2:19][N:14]([CH2:13][C:12]([OH:11])=[O:26])[C:15](=[O:25])[C@@H:16]1[CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:51])[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:45]=1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10784543N-benzyloxycarbonyl-4-methoxycarbonyl-L-phenylalanineHCID 70048775HCID 70048775, compound

Product 1

HCID 53692132HCID 53692132, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 7.6 ml of methylene chloride were dissolved 0.76 g of (S)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid t butyl ester oxalic acid salt and 0.47 g of N-benzyloxycarbonyl-4-methoxycarbonyl-L-phenylalanine. To the solution was added gradually, while cooling with water, 0.44 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide, over 5 minutes. The mixture was stirred for one hour at room temperature, then methylene chloride was distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed with a 5% aqueous solution of potassium hydrogensulfate and a saturated aqueous solution of hydrogencarbonate. The organic layer was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by means of a silica gel chromatography (hexane/ethyl acetate=l/2) to give 0.46 g (51.1%) of the title compound as a colorless oily product.

Workup

  1. additionTo the solution was added gradually
  2. distillationmethylene chloride was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe solution was washed with a 5% aqueous solution of potassium hydrogensulfate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified by means of a silica gel chromatography (hexane/ethyl acetate=l/2)

Sources & evidence

ORD record
ord-ba1ca03f12df44af8180467148738fa9
Source dataset
uspto-grants-1996_08
Patent number
US05550131

Reaction notes

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