Potassium bisulfate → tert-Butyl (S,S)-[4-(2-benzyloxycarbonylamino-propionyl)-3-methoxycarbonylmethyl-2-oxopiperazin-1-yl]acetate

HRID 1066559Notes

Reaction equation

HRID 1066559 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C@@H:6]1[NH:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:7]1=[O:20])=[O:4].[CH2:21]([O:28][C:29]([NH:31][C@H:32]([C:34](O)=[O:35])[CH3:33])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.C(N=C=NCCCN(C)C)C.S([O-])(O)(=O)=O.[K+]>C(#N)C>[CH2:21]([O:28][C:29]([NH:31][C@@H:32]([CH3:33])[C:34]([N:11]1[CH2:10][CH2:9][N:8]([CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C:7](=[O:20])[C@@H:6]1[CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:35])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 516920Potassium bisulfateHCID 736104N-carbobenzyloxyalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10636945HCID 10636945, compound

Product 1

HCID 15521376tert-Butyl (S,S)-[4-(2-benzyloxycarbonylamino-propionyl)-3-methoxycarbonylmethyl-2-oxopiperazin-1-yl]acetateYield 74.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (S)-(3-methoxycarbonylmethyl-2-oxo-piperazin-1-yl)acetate (3.0 g) and benzyloxycarbonyl-L-alanine (2.61 g) were dissolved in acetonitrile (40 ml). While stirring the solution at room temperature, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.45 g) was added to the solution, and the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into a 5% aqueous solution of potassium hydrogen sulfate and the solution was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate and dried over anhydrous magnesium sulfate (MgSO4). The solution was concentrated under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent:hexane:ethyl acetate=1:4) to give the titled compound (3.83 g) as a pale yellow amorphous powdery product.

Workup

  1. stirringthe mixture was stirred for 3 hours at room temperature
  2. extractionthe solution was extracted with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  5. concentrationThe solution was concentrated under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (eluent:hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-353f3e734a84426d8a4aef0315a5a217
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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