Butyl isocyanate → HCID 86584842, compound

HRID 1006797Notes

Reaction equation

HRID 1006797 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([S:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][NH:6]1)=[N+:2]=[N-:3].[CH2:30]([N:34]=[C:35]=[O:36])[CH2:31][CH2:32][CH3:33]>C1COCC1>[CH2:30]([NH:34][C:35]([N:6]1[CH2:7][C@H:8]([S:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:9][C@H:5]1[CH2:4][N:1]=[N+:2]=[N-:3])=[O:36])[CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 11269582HCID 11269582, compound

Product 1

HCID 86584842HCID 86584842, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

280 mg (0.7 mmol) (2S,4R)-2-azidomethyl-4-tritylsulfanyl-pyrrolidine were treated with 87 μM (0.77 mol, 1.1 eq) butyl isocyanate in 5 ml THF at 0° C., and the solution was stirred at RT for 45 min. The solvent was evaporated, and the residue was purified by flash chromatography yielding 278 mg (80%) (2S,4R)-2-azidomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butylamide as white foam.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-153b81f7a5a9403fb0b54b48281eb291
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

Loading…