Hydrochloric Acid → 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester

HRID 22969

반응식

HRID 22969 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4](/[CH:7]=[CH:8]/[C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[N:3]1[CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.Cl>C1(C)C=CC=CC=1.CO>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][S:18][CH2:17][CH2:16][N:3]1[C:2](=[O:1])[CH2:6][CH2:5][C@@H:4]1/[CH:7]=[CH:8]/[C@@H:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 12132851methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl] pyrrolidin-1-yl}ethyl)thio]-butanoate

생성물 1

HCID 121328524-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester수율 29.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

반응 조건

온도
-30 °C

실험 절차

A solution of methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl]pyrrolidin-1-yl}ethyl)thio]-butanoate (0.039 g, 0.1 mmol) in 2 mL of anhydrous toluene was added dropwise to a −30° C. solution of (R)-2-methyl-CBS-oxazaborolidine (1 M in toluene, 0.05 mL, 0.05 mmol) and borane-methyl sulfide complex (10 M, 0.01 mL, 0.1 mmol). The reaction was stirred for 7 hours at −30° C. and then a solution of hydrochloric acid in methanol (2 M, 1-2 mL) was added. The solution was warmed to room temperature and the solvents were removed via reduced pressure. The crude residue was purified via chromatography yielding 11 mg of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester as an oil. This was taken directly on to the next step.

후처리

  1. temperatureThe solution was warmed to room temperature
  2. customthe solvents were removed via reduced pressure
  3. customThe crude residue was purified via chromatography

출처 및 근거

ORD 기록
ord-8aa5e02b8b4542b18d3d5fa4e489be9c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849657B2

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