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Hydrochloric Acid → Tert-butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoate

HRID 1007862
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HRID 1007862 반응식
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].Cl.[CH2:11]([O:18][CH2:19][C:20]1[C:21]([O:30][CH3:31])=[N:22][CH:23]=[CH:24][C:25]=1[C:26](=[O:29])[CH2:27][CH3:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1.[Zn]>[CH2:11]([O:18][CH2:19][C:20]1[C:21]([O:30][CH3:31])=[N:22][CH:23]=[CH:24][C:25]=1[C:26]([OH:29])([CH2:27][CH3:28])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 105411281-(3-Benzyloxymethyl-2-methoxy-pyridin-4-yl)-propan-1-one

생성물 1

HCID 10834902Tert-butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoate수율 95%

시약·촉매·용매 2

HCID 23994
Zinc
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

tert-butyl bromoacetate (13 ml, 80 mmol) is added dropwise to a zinc suspension (5.3 g, 80 mmol activated with 6N HCl over 10 seconds, then washed successively with water until a neutral pH is achieved, with acetone and with diethyl ether) in anhydrous tetrahydrofuran (60 ml) under reflux. The reaction medium is maintained under reflux for another 10 minutes after the addition is terminated. Then, a solution of 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone (5.8 g, 20 mmol) in anhydrous tetrahydrofuran (20 ml) is added and the reaction mixture is agitated under reflux for another hour. The reaction is stopped at 0° C. with saturated aqueous ammonium chloride (100 ml) and the reaction mixture is extracted with diethyl ether. The combined extracts are dried over sodium sulphate and evaporated, which produces a yellow oil which is purified by column chromatography (SiO2, TBMO/HX: 5/95 to 10/90) in order to obtain the tert-butyl ester (J) (7 g, 95%) in the form of a limpid liquid.

후처리

  1. washwashed successively with water until a neutral pH
  2. temperatureunder reflux
  3. temperatureThe reaction medium is maintained
  4. temperatureunder reflux for another 10 minutes
  5. additionafter the addition
  6. customis terminated
  7. temperatureunder reflux for another hour
  8. extractionthe reaction mixture is extracted with diethyl ether
  9. dry with materialThe combined extracts are dried over sodium sulphate
  10. customevaporated
  11. customwhich produces a yellow oil which
  12. customis purified by column chromatography (SiO2, TBMO/HX: 5/95 to 10/90) in order

출처 및 근거

ORD 기록
ord-5e6a206c6e4042338c07002ba77ce101
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06797715B1

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