5-Aminosalicylic Acid → Boc-Lys(Z)-OH

HRID 364613노트

반응식

HRID 364613 반응식
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].N[C:29]1C=[C:33](C(O)=O)[C:32]([OH:38])=[CH:31]C=1.CN(C=O)C>C1COCC1>[CH3:29][CH2:21][O:23][CH2:24][CH3:27].[CH:2]([O:38][CH:32]([CH3:31])[CH3:33])([CH3:18])[CH3:3].[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

참가 물질

6

반응물 3

HCID 40755-Aminosalicylic AcidHCID 6228DimethylformamideHCID 2724765Boc-Lys(Z)-OH

생성물 2

HCID 2724765Boc-Lys(Z)-OH수율 55%HCID 21919906Ether isopropyl ether

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

70.4 g (0.14 mole) of BOC-L-Lys(Z)-SDP (m.w. 502.6) was dissolved in 200 ml of THF, which was then added dropwise to a solution of 21.4 g (0.14 mole) of 5-aminosalicylic acid (m.w. 153.14) in 187 ml of 1.5N NEM/DMF solution at 0°-5° C., and the reaction was effected at normal temperature for 18 hours, after which the reaction mixture was concentrated to 100-200 ml, 1600 ml of ether/ethyl acetate (50 v/50 v) was added, the mixture was washed with 1000 ml of cold 5% HCl three times and then with 1000 ml of saturated aqueous NaCl twice, active carbon was added, dried on magnesium sulfate, and the solvent was distilled off, to obtain, by recystallization from ether/isopropyl ether, 8.9 g (yield 55%) of crystalline BOC-L-Lys(Z)-CHA (m.w. 515.6) of m.p. 102°-105° C.

후처리

  1. concentrationafter which the reaction mixture was concentrated to 100-200 ml, 1600 ml of ether/ethyl acetate (50 v/50 v)
  2. additionwas added
  3. washthe mixture was washed with 1000 ml of cold 5% HCl three times
  4. additionwith 1000 ml of saturated aqueous NaCl twice, active carbon was added
  5. customdried on magnesium sulfate
  6. distillationthe solvent was distilled off

출처 및 근거

ORD 기록
ord-94033bd2694a4121926a3cc0f69377af
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605614

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