1,3-Propanedithiol → HCID 131718394, compound

HRID 1464352Notes

Reaction equation

HRID 1464352 reaction equation
C(S)CCS.[CH2:6]([O:8][P:9]([CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])([CH:11]([N:24]=[N+]=[N-])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[CH3:7].C(N(CC)CC)C>CO>[CH2:6]([O:8][P:9]([CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])([CH:11]([NH2:24])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 131718395HCID 131718395, compound

Product 1

HCID 131718394HCID 131718394, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.04 ml of 1,3-propanedithiol were added dropwise to a stirred solution of 3.65 g of benzyl 2(R or S)-[[(RS)-(ethoxy)[1-(RS)-azido-5-tert.butoxycarbonylaminopentyl]phosphinyl]methyl]-4-methylvalerate and 2.83 ml of triethylamine in 80 ml of methanol. The mixture was stirred at room temperature overnight, the solvent was removed by evaporation and the residue was purified by flash chromatography on silica gel using 4% methanol/dichloromethane for the elution to give 3.25 g of benzyl 2(R or S)-[[(RS)-(ethoxy)[1-(RS)-amino-5-tert.butoxy carbonylaminopentyl]phosphinyl]methyl]-4-methylvalerate as an off-white foam; nmr (CDCl3): 7.36 (s,5H); 5.2-5.08 (m,2H); 4.6 (brs,1H); 4.2-3.98 (m,2H); 3.17-3.08 (m,2H); 3.0-2.76 (m,2H); 2.4-2.13 (m,1H): 2.0-1.25 (m,25H); 0.98-0.86 (m,6H); MS: 513 (M+H)+.

Workup

  1. customthe solvent was removed by evaporation
  2. customthe residue was purified by flash chromatography on silica gel using 4% methanol/dichloromethane for the elution

Sources & evidence

ORD record
ord-fc8b3c4e24c6475184a79061e1c1b454
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

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