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

HRID 1034510ノート

反応式

HRID 1034510 の反応式
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]

参加物

8

反応物 5

HCID 11776TriphenylphosphineHCID 82267SulfamideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 107265421,1-Dimethylethyl N-(aminosulfonyl)carbamateHCID 57080293tert-Butyl (2R,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9230b6033b8e4896b06467b63b36f1fb
出典データセット
uspto-grants-1994_05
特許番号
US05317016

反応ノート

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