Sulfuric Acid → HCID 10354452, compound

HRID 1289101Notes

Reaction equation

HRID 1289101 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=[O:15].S([O-])([O-])(=O)=O.C[N+](C)(C)C.C[N+](C)(C)C.S(=O)(=O)(O)O>ClCCl.C(=O)([O-])O.[Na+]>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([OH:16])=[O:15])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 801724-Cyanobenzoyl chlorideHCID 145742L-ProlineHCID 14746849Bis(N,N,N-trimethylmethanaminium) sulfate

Product 1

HCID 10354452HCID 10354452, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4.97 g of 4-cyanobenzoyl chloride, 3.45 g of L-proline and 0.73 g of tetramethylammonium sulphate in 300 ml of dichloromethane and 150 ml of 5% sodium hydrogen carbonate solution are stirred for 48 hours. The aqueous phase is acidified with 3N sulphuric acid and extracted with ethyl acetate. The ethyl acetate phase is washed with saturated sodium chloride solution, dried and evaporated. Chromatography of the residue on silica gel (RP-18) using water gives 3.70 g of 1-(p-cyanobenzoyl)-L-proline. M.p. 80°-85° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate phase is washed with saturated sodium chloride solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c3072734fde14738933246f26f178e94
Source dataset
uspto-grants-1998_05
Patent number
US05747522

Reaction notes

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