(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → (S)-tert-Butyl 2-((S)-1-cyano-2-(4-iodophenyl)ethylcarbamoyl)piperidine-1-carboxylate

HRID 600292Notes

Reaction equation

HRID 600292 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:12][C:13]([C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C(Cl)Cl>[C:2]([C@@H:3]([NH:12][C:13]([C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 57999641(S)-tert-Butyl 2-((S)-1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 57999629(S)-tert-Butyl 2-((S)-1-cyano-2-(4-iodophenyl)ethylcarbamoyl)piperidine-1-carboxylateYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 2-((S)-1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate (2.88 g) was dissolved in DCM (40 mL) and to the solution was added (methoxycarbonylsulfamoyl)triethyl ammonium hydroxide (3.42 g). The reaction mixture was stirred under nitrogen, at room temperature overnight, then concentrated in vacuo. Crude material was purified by flash silica chromatography eluting with 20% ethyl acetate in isohexane to give the title compound (2.7 g) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customCrude material was purified by flash silica chromatography
  3. washeluting with 20% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-0dffb4665b084b048f4a37810f21d911
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

Loading…