Chlorotrimethylsilane → HCID 57030967, 화합물

HRID 1034526노트

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HRID 1034526 반응식
[NH2:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([SH:8])[CH2:5][N:4]1[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10].C(N(CC)CC)C.C[Si](C)(C)Cl.[S:27](Cl)(=[O:30])(=[O:29])[NH2:28]>ClCCl>[CH2:12]([O:11][C:9]([N:4]1[CH2:5][C@@H:6]([SH:8])[CH2:7][C@H:3]1[CH2:2][NH:1][S:27](=[O:30])(=[O:29])[NH2:28])=[O:10])[CH:13]=[CH2:14]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine3회HCID 24499Chlorosulfamic acidHCID 572801191-Pyrrolidinecarboxylic acid, 2-(aminomethyl)-4-mercapto-, 2-propenyl ester, (2S-cis)-

생성물 1

HCID 57030967HCID 57030967, 화합물수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (2S,4S)-2-aminomethyl-1-allyloxycarbonyl-4-mercaptopyrrolidine (2.80 g: ca. 13.14 mmole) in dichloromethane (66 ml) at -50° C., triethylamine (4.02 ml: 28.91 mmole) and trimethylchlorosilane (3.76 ml: 28.91 mmole) are added dropwise over 15 minutes. The mixture is stirred at the same temperature for 20 minutes. To the reaction mixture triethylamine (0.92 ml: 6.57 mmole) and a solution of sulfamoyl chloride (19.37 mmole) in dichloromethane (6.8 ml) are added dropwise over 20 minutes at -70° C., and the mixture is stirred for 30 minutes. To the reaction mixture triethylamine (3.84 ml: 27.59 mmole) is again added over 1 hour at -50° C. The reaction mixture is kept at the same temperature overnight and concentrated in vacuo. The residual oil is purified by silica gel chromatography (ethyl acetate) to give (2S,4S)-1-allyloxycarbonyl-2-(sulfamoylamino)methyl-4-mercaptopyrrolidine (2.64 g). Yield: 68%. White powder. NMR δ(CDCl3) ppm: 1.4 to 1.6(m, 1H), 1.83(d, J=6.2 Hz, 1H), 2.5 to 2.7(m, 1H), 3.11(dd, J=8.2 Hz, J=11.6 Hz, 1H), 3.3 to 3.4(m, 1H), 3.71(dd, J=2.9 Hz, J=15.2 Hz, 1H), 4.13(dd, J=7.3 Hz, J=11.7 Hz, 1H), 4.16(dd, J=10.3, 14.9 Hz, 1H), 4.3 to 4.6 (m, 3H), 4.7(m, 2H), 5.2 to 5.4(m, 4H), 5.8 to 6.0(m, 2H), 6.0(m, 2H). IR ν (CHCl3) cm-1 : 1684, 1158.

후처리

  1. stirringthe mixture is stirred for 30 minutes
  2. customis kept at the same temperature overnight
  3. concentrationconcentrated in vacuo
  4. customThe residual oil is purified by silica gel chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-2976adc0ed8b4b93a64720a544212b08
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05317016

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