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

HRID 1034510노트

반응식

HRID 1034510 반응식
S(N)(N)(=O)=O.[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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43]([O:47][C:48]([NH:50][S:51]([NH2:54])(=[O:53])=[O:52])=[O:49])([CH3:46])([CH3:45])[CH3:44].C(OC(N=NC(OCC)=O)=O)C>O1CCCC1.C1(C)C=CC=CC=1>[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:50]([C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:49])[S:51](=[O:52])(=[O:53])[NH2:54])[CH2:11]1)(=[O:8])[CH3:7]

참가 물질

8

반응물 5

HCID 11776TriphenylphosphineHCID 82267SulfamideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 107265421,1-Dimethylethyl N-(aminosulfonyl)carbamateHCID 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 2

HCID 1140Toluene용매HCID 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. NMR δ(CDCl3) ppm: 1.41(s, 9H), 1.55(s, 9H), 1.19 to 2.0(m, 2H), 2.35(s, 3H), 3.32(dd, J=11.4 Hz, J=8.2 Hz, 1H), 3.6 to 3.9(m, 3H), 3.9 to 4.1(m, 1H), 4.5(m, 1H), 6.15(s, 2H). IR ν (KBr) cm-1 : 3420, 3320, 1706, 1686, 1666.

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-9230b6033b8e4896b06467b63b36f1fb
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05317016

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