4-Toluenesulfonyl chloride → N-(p-toluenesulphonyl)-L-alanyl-L-proline anilide

HRID 1448734Notes

Reaction equation

HRID 1448734 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].[OH-].[Na+].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([NH:2][C@H:3]([C:5]([N:7]2[CH2:20][CH2:19][CH2:18][C@H:8]2[C:9]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[O:6])[CH3:4])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 22809936L-alanyl-L-proline anilide hydrobromide

Product 1

HCID 40223683N-(p-toluenesulphonyl)-L-alanyl-L-proline anilideYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.71 g (0.005 mol) of L-alanyl-L-proline anilide hydrobromide were suspended in 20 ml of dichloromethane. To the suspension were added 22 ml of 0.5-N sodium hydroxide solution followed by 1.05 g (1.1 equivalents) of p-toluenesulphonyl chloride. The mixture was stirred vigorously for 90 minutes. 50 ml of dichloromethane were added, the organic layer was separated, washed with 50 ml of brine, dried over magnesium sulphate and evaporated to an oil which crystallised upon the addition of petroleum ether. The solid was filtered off, washed with petroleum ether and dried to yield 1.94 g (93%) of N-(p-toluenesulphonyl)-L-alanyl-L-proline anilide of melting point 145°-147° C.; [α]D20 =-126.2° (c=1.00% in glacial acetic acid).

Workup

  1. customthe organic layer was separated
  2. washwashed with 50 ml of brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to an oil which
  5. customcrystallised upon the addition of petroleum ether
  6. filtrationThe solid was filtered off
  7. washwashed with petroleum ether
  8. customdried

Sources & evidence

ORD record
ord-2137aa1edc914379a9f196c71edde885
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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