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

HRID 1448734노트

반응식

HRID 1448734 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2137aa1edc914379a9f196c71edde885
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04187216

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