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Diethyl Ether → Ethyl 2,6-difluoro-4-[(3-hydroxy-4-chloro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

HRID 1935657
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HRID 1935657 반응식
[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[C:25]([OH:26])=[CH:24][C:23]3[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:30])([CH3:29])[C:18]=3[CH:17]=2)=[O:15])[CH:10]=[C:9]([F:31])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:35])(=O)=O.C(OCC)C>ClCCl>[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[C:25]([OH:26])=[C:24]([Cl:35])[C:23]3[C:22]([CH3:28])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:30])([CH3:29])[C:18]=3[CH:17]=2)=[O:15])[CH:10]=[C:9]([F:31])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]
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참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 24648Sulfuryl chlorideHCID 22465056Ethyl 2,6-difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate2회

생성물 1

HCID 10298591Ethyl 2,6-difluoro-4-[(3-hydroxy-4-chloro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution ethyl 2,6-difluoro-4-[(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate (Compound C, 227 mg, 0.52 mmol) in 10 ml of anhydrous dichloromethane under nitrogen at 25° C. was added sulfuryl chloride (0.0413 ml, 0.57 mmol) and anhydrous ethyl ether (0.054 ml, 0.52 mmol). Reaction was instantaneous at 25° C. as monitored by 1H NMR. The reaction mixture was quenched with saturated NaHCO3 then extracted with ethyl acetate. The organic layer was washed with water, brine and dried over Na2SO4. The title compound was obtained as a white solid after column chromatography with ethyl acetate:hexane (1:9).

후처리

  1. customReaction
  2. customwas instantaneous at 25° C.
  3. customThe reaction mixture was quenched with saturated NaHCO3
  4. extractionthen extracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-6abf7bc3a4384040ac155343446acb96
출처 데이터셋
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06387950B2

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