Triphenylphosphine → HCID 56639408, compound

HRID 1088257Notes

Reaction equation

HRID 1088257 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15](O)[CH2:14][C@H:13]2[CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[O:20])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:64]([OH:67])(=[S:66])[CH3:65]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:66][C:64](=[O:67])[CH3:65])[CH2:14][C@H:13]2[CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[O:20])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15671444HCID 15671444, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 56639408HCID 56639408, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-p-methoxybenzyloxycarbonylmethyl-4-hydroxypyrrolidine (1.40 g) and triphenylphosphine (1.18 g) were dissolved in 7 ml of dry tetrahydrofuran under nitrogen stream. To the resulting solution was added 783 mg of diethyl azodicarboxylate at 0° C., followed by stirring at the same temperature for 30 minutes. Thereafter, 342 mg of thioacetic acid was added thereto, and the mixture was stirred for 1 hour. The reaction mixture was diluted with ethyl acetate, washed successively with a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography to give (2R,4S)-1-(p-nitrobenzyl-oxycarbonyl)-2-p-methoxybenzyloxycarbonylmethyl-4-acetylthiopyrrolidine.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. washwashed successively with a saturated sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef6e9017e80b424580b200e0415328c9
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

Loading…