Methyl iodide → Racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodide

HRID 1811081노트

반응식

HRID 1811081 반응식
[Br:1][C:2]1[C:3]([CH3:27])=[C:4]([NH:8][C:9](=[O:26])[CH:10]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:12][S:13][CH3:14])[CH:5]=[CH:6][CH:7]=1.[I:28][CH3:29]>C(Cl)Cl>[I-:28].[CH2:18]([O:17][C:16]([NH:15][CH:10]([C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[CH3:27])=[O:26])[CH2:11][CH2:12][S+:13]([CH3:29])[CH3:14])=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

4

반응물 2

HCID 6328Methyl iodideHCID 66606795Racemic benzyl 1-(3-bromo-2-methylphenylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate

생성물 1

HCID 87071307Racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodide수율 101.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Step 2 A mixture of racemic benzyl 1-(3-bromo-2-methylphenylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate (1.31 g, 2.90 mmol) and DCM (4 mL) was diluted with iodomethane (7.5 mL, 120 mmol) and the mixture was stirred at rt. After 24.5 h, the mixture (a solution with an insoluble reddish oil) was concentrated under vacuum. The residue was treated three times with DCM and concentrated under vacuum to provide racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodide as an orange-yellow glassy foam (1.75 g, 97%). 1H NMR (400 MHz, chloroform-d) δ9.16 (1H, br. s.), 7.28-7.46 (7H, m), 6.99 (1H, t, J=8.0 Hz), 6.71 (1H, d, J=6.8 Hz), 5.11 (2H, s), 4.84 (1H, br. s.), 3.75 (1H, br. s.), 3.54 (1H, br. s.), 3.14 (3H, br. s.), 2.96 (3H, s), 2.75 (1H, br. s.), 2.33-2.41 (1H, m), 2.30 (3H, br. s.). Mass spectrum m/z 465, 467 (M)+.

후처리

  1. concentrationthe mixture (a solution with an insoluble reddish oil) was concentrated under vacuum
  2. additionThe residue was treated three times with DCM
  3. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-9b21edc0fcf74f899316754b436141c6
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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