Acetic Anhydride → N-acetyl-L-alanyl-L-proline anilide

HRID 1448730Notes

Reaction equation

HRID 1448730 reaction equation
Br.[NH2:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])=[O:6])[CH3:4].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([NH:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:10])=[O:6])[CH3:4])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22809936L-alanyl-L-proline anilide hydrobromide

Product 1

HCID 54044650N-acetyl-L-alanyl-L-proline anilideYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2 g (0.00585 mol) of L-alanyl-L-proline anilide hydrobromide were dissolved in 40 ml of dry pyridine and 1.1 ml (0.0117 mol) of acetic anhydride were added. The solution was stirred at room temperature for 1 hour and then evaporated. Final traces of pyridine were removed by addition of 20 ml of toluene ane re-evaporation. The residue was dissolved in 100 ml of chloroform and the solution washed with 80 ml of saturated sodium chloride solution, dried over magnesium sulphate and evaporated to an oil. This oil crystallised from ethyl acetate/petroleum ether to give 1.64 g (93%) of N-acetyl-L-alanyl-L-proline anilide of melting point 163°-165° C.; [α]D20 =-186.2° (c=1.022% in methanol).

Workup

  1. customevaporated
  2. customwere removed by addition of 20 ml of toluene ane re-evaporation
  3. dissolutionThe residue was dissolved in 100 ml of chloroform
  4. washthe solution washed with 80 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to an oil
  7. customThis oil crystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-0d1edfc6d0cb425188370c6e638c484a
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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