Water → (+/-)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester

HRID 1838422노트

반응식

HRID 1838422 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:23][C:24](=[O:47])[CH:25]([CH2:44][CH2:45]O)[N:26]([CH3:43])[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:21]=[CH2:22].C(Br)(Br)(Br)[Br:49].O>O1CCCC1>[CH2:20]([O:23][C:24](=[O:47])[CH:25]([CH2:44][CH2:45][Br:49])[N:26]([CH3:43])[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:21]=[CH2:22]

참가 물질

6

반응물 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18753502(+/-)-2-(2-hydroxyethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester

생성물 1

HCID 18753632(+/-)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester수율 86.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

After triphenylphosphine (4.72 g, 18.0 mmol) was added to a solution of (±)-2-(2-hydroxyethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester (6.08 g, 15.0 mmol), the product of Example 41(2), in tetrahydrofuran (45 ml), a solution of carbon tetrabromide (5.97 g, 18.0 mmol) in tetrahydrofuran (20 ml) was added over 20 minutes to the solution with ice-cooling and with stirring. The mixture was stirred at room temperature for 1 hour. To the reaction mixture, water was added and this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=5/1 as the eluant to afford the desired compound (6.05 g, yield 86%) as a colorless oil.

후처리

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionthis was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-af34643bd05f4683b4b63428bc71cda1
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06673804B1

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