4-Methoxybenzyl alcohol → HCID 10605273, 화합물

HRID 1941568노트

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HRID 1941568 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

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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%.

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-38aa48ca617f489fa3f21884a69e2865
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703243

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