Sodium Chloride → O-Benzyl-N-benzyloxycarbonyltyrosinol

HRID 5725

반응식

HRID 5725 반응식
C[O:2][C:3](=O)[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[Cl-].[Li+].[BH4-].[Na+].[Cl-].[Na+]>C(O)C.O1CCCC1>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][C@@H:4]([CH2:3][OH:2])[NH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:18][CH:19]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 10916769O-benzyl-N-benzyloxycarbonyltyrosine methyl ester

생성물 1

HCID 22863341O-Benzyl-N-benzyloxycarbonyltyrosinol수율 99.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

27.25 g of O-benzyl-N-benzyloxycarbonyltyrosine methyl ester was dissolved in a mixed solvent of 185 ml of ethanol and 122 ml of tetrahydrofuran, and to the solution were added 5.8 g of lithium chloride and 5.2 g of sodium borohydride under ice cooling. The reaction mixture was stirred at a room temperature for 18 hours, and after the addition of 500 ml of saturated sodium chloride aqueous solution, extracted twice with 300 ml of chloroform. The extract was dried over magnesium sulfate and concentrated under a reduced pressure to obtain 25.4 g of the title compound as colorless crystals

후처리

  1. extractionextracted twice with 300 ml of chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-915998a24bba4f2190531cc7ca53e3a6
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245034

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