4-Toluenesulfonyl chloride → Trp(Tos)-OBzl

HRID 1649339

반응식

HRID 1649339 반응식
[NH2:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[H-].[Na+].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(OCC)(=O)C>CN(C)C=O.O>[NH2:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[CH:5]=1

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 7016092L-Tryptophan benzyl ester

생성물 1

HCID 131713224Trp(Tos)-OBzl

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

In N,N-dimethylformamide (DMF) (10 ml) was dissolved Tr-Trp-OBzl (2.15 g, 4 mM), followed by addition of sodium hydride (50% in mineral oil, the same applies below; 240 mg, 5 mM) in a nitrogen gas stream. The reaction was conducted at room temperature for 20 minutes, after which p-toluenesulfonyl chloride (950 mg, 5 mM) was added. The reaction was further carried out at room temperature for 15 hours, at the end of which time ethyl acetate (50 ml) was added and the mixture was stirred for one hour. To the reaction mixture was added water (30 ml) with caution and the organic layer was taken and washed with 5% aqueous sodium hydrogen carbonate and water. After drying over sodium sulfate, the ethyl acetate was distilled off. The residue was purified by column chromatography on silica gel (15 g) using toluene as the solvent to give Tr-Trp(Tos)-OBzl. Yield 1.70 g (61.5%); m.p. 101°-103° C.; [α]D24 +47.6° (c=0.5, DMF).

후처리

  1. additionwas added
  2. washwashed with 5% aqueous sodium hydrogen carbonate and water
  3. dry with materialAfter drying over sodium sulfate
  4. distillationthe ethyl acetate was distilled off
  5. customThe residue was purified by column chromatography on silica gel (15 g)

출처 및 근거

ORD 기록
ord-238004af3a314d198c685971ec4c51f1
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04416820

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