Toluene → (2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine

HRID 1941604노트

반응식

HRID 1941604 반응식
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].[C:6]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH2:22]O)[CH2:11]1)(=[O:8])[CH3:7].C([O:26][C:27](N=NC(OCC)=O)=[O:28])C.[C:36]1([CH3:42])[CH:41]=CC=C[CH:37]=1>O1CCCC1>[C:6]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C@@H:12]([CH2:22][N:4]([C:27]([O:28][C:36]([CH3:42])([CH3:41])[CH3:37])=[O:26])[S:1](=[O:3])(=[O:2])[NH2:5])[CH2:11]1)(=[O:8])[CH3:7]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 82267SulfamideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57080293tert-Butyl (2R,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 57156698(2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Preparation of a sulfamide compound To a solution of (2R,4S)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (i.e., a substrate) in tetrahydrofuran (THF) triphenylphosphine (PPh3) N-t-butoxycarbonylsulfamide (BSMD), and azodicarboxylic acid diethyl ester (DEAD) are successively added under ice cooling. The conditions for this reaction are shown in Table 2, Step A-6. The reaction mixture is diluted with toluene, concentrated, diluted with toluene, and the formed crystals are filtered off. The filtrate is concentrated. The residue is purified by silica gel column chromatography to give (2R,4S)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine.

후처리

  1. concentrationconcentrated
  2. additiondiluted with toluene
  3. filtrationthe formed crystals are filtered off
  4. concentrationThe filtrate is concentrated
  5. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5ee6fa901ec94c91b0569f27dfffb32f
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703243

반응 노트

불러오는 중…