4-Methoxybenzyl alcohol → HCID 10605273, 화합물

HRID 1034475노트

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HRID 1034475 반응식
ClS(N=C=O)(=O)=O.COC1C=CC(CO)=CC=1.[CH3:18][O:19][C:20]1[CH:34]=[CH:33][C:23]([CH2:24][O:25][C:26]([NH:28][S:29](Cl)(=[O:31])=[O:30])=[O:27])=[CH:22][CH:21]=1.[CH3:35][O:36][C:37]1[CH:73]=[CH:72][C:40]([CH2:41][O:42][C:43]([N:45]2[CH2:49][C@@H:48]([S:50][C:51]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH2:47][C@H:46]2[CH2:70][NH2:71])=[O:44])=[CH:39][CH:38]=1.C(N(CC)CC)C>ClCCl>[CH3:35][O:36][C:37]1[CH:38]=[CH:39][C:40]([CH2:41][O:42][C:43]([N:45]2[CH2:49][C@@H:48]([S:50][C:51]([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)([C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH2:47][C@H:46]2[CH2:70][NH:71][S:29](=[O:31])(=[O:30])[NH:28][C:26]([O:25][CH2:24][C:23]2[CH:33]=[CH:34][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[O:27])=[O:44])=[CH:72][CH:73]=1

참가 물질

7

반응물 5

HCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 10578323HCID 10578323, 화합물HCID 21461338Carbamic acid, (chlorosulfonyl)-, (4-methoxyphenyl)methyl ester

생성물 1

HCID 10605273HCID 10605273, 화합물수율 91.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-50 °C

실험 절차

To a solution of chlorosulfonyl isocyanate (3.95 ml: 45.4 mmole) in dichloromethane (70 ml), p-methoxybenzyl alcohol (5.66 ml: 45.4 mmole) is added at -50° C. The mixture is stirred at -50° C. for 15 minutes. The resulting solution of p-methoxybenzyloxycarbonylsulfamoyl chloride is added to a solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-aminomethyl-4-tritylthiopyrrolidine (obtained in the above Steps 6 or 8) (12.21 g: 22.7 mmole) and triethylamine (6.38 ml: 45.6 mmole) in dichloromethane (300 ml) at -78° C., and the mixture is stirred for 10 minutes, successively washed with dilute hydrochloric acid and brine, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-p-methoxybenzyloxycarbonylsulfamoylaminomethyl-4-tritylthiopyrrolidine (16.31 g). Yield: 91.6%. NMR δ(CDCl3) ppm: 3.78(s, 3H), 3.81, 3.83(2×s, 3H), 4.98, 4.89(ABq, J=12 Hz, 2H), 5.09, 5.03(ABq, J=12 Hz, 2H). IR ν (CHCl3) cm-1 : 3390, 1740, 1685.

후처리

  1. stirringthe mixture is stirred for 10 minutes
  2. washsuccessively washed with dilute hydrochloric acid and brine
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-eb1f030231ce4d239c6c049352c5f221
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05317016

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