Tyrosol → Tert-butyl [4-(2-hydroxyethyl)phenoxy]acetate

HRID 458500

반응식

HRID 458500 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]([O:15][C:13]([CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

5

반응물 3

HCID 10393Tyrosol2회HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

생성물 1

HCID 23119602Tert-butyl [4-(2-hydroxyethyl)phenoxy]acetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

The hapten p-(carboxymethyl)ritodrine (Hapten E) was prepared in four steps according to FIG. 7 of the accompanying drawings, from 2-(4-hydroxyphenyl)ethanol 17. The reaction of 17 with t-butyl bromoacetate in acetonitrile in the presence of potassium carbonate at 60° C. gives 2-[4-(t-butoxycarbonylmethoxy)phenyl]ethanol 18. The oxidation of the alcohol 18 with pyridinium chlorochromate (pcc) in dichloromethane gives the 2-[4-(t-butoxycarbonylmethoxy)phenyl]ethanal 19. The ester 20, obtained by condensation of the aldehyde 19 with α-(1-aminoethyl)-4-hydroxybenzyl alcohol hydrochloride 13 in methanol in the presence of sodium cyanoborohydride and triethylamine. Deprotection of the t-butyl protecting group of the ester 20 with 4 M HCl in dioxane at room temperature gave Hapten E in moderate yield.

출처 및 근거

ORD 기록
ord-840cea4db1a04a7d8d622476971a7924
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192722B2

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