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

HRID 1941604Notes

Reaction equation

HRID 1941604 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5ee6fa901ec94c91b0569f27dfffb32f
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

Loading…