Triphenylphosphine → HCID 57304174, compound

HRID 1078730Notes

Reaction equation

HRID 1078730 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](O)[CH2:10][C@H:9]1[C@H:14]([OH:26])[CH2:15][CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:58]([OH:61])(=[S:60])[CH3:59]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:60][C:58](=[O:61])[CH3:59])[CH2:10][C@H:9]1[C@H:14]([OH:26])[CH2:15][CH2:16][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH3:18])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10761953HCID 10761953, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 57304174HCID 57304174, compoundYield 680.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-2-[(R)-3-(N-tert-butoxycarbonyl-N-methylamino)-1-hydroxypropyl]-4-hydroxypyrrolidine (1.0 g, 2.67 mmol, intermediate prepared in REFERENCE EXAMPLE 27-2) in tetrahydrofuran (10 ml) were successively added triphenylphosphine (842 mg, 3.21 mmol) and diethyl azodicarboxylate (0.505 ml, 3.21 mmol) under a nitrogen atmosphere under cooling with ice. The mixture was stirred at the same temperature for 10 minutes, and then thioacetic acid (0.25 ml, 0.35 mmol) was dropwise added thereto. The reaction solution was stirred at the same temperature for 2.5 h and then concentrated in vacuo. A mixture (10 ml) of hexane-ethyl acetate (5:1) was added to the residue. The precipitate was filtered off, and the filtrate was concentrated in vacuo. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, hexane-ethyl acetate=5:1) to give (2S,4R)-N-tert-butoxycarbonyl-4-acetylthio-2-[(R)-3-(N-tert-butoxycarbonyl-N-methylamino)-1-hydroxypropyl]pyrrolidine (1.03 g, yield: 89.2%). The data of this compound agreed with those of the compound prepared in REFERENCE EXAMPLE 27-2. ##STR411##

Workup

  1. temperatureunder cooling with ice
  2. stirringThe reaction solution was stirred at the same temperature for 2.5 h
  3. concentrationconcentrated in vacuo
  4. additionA mixture (10 ml) of hexane-ethyl acetate (5:1) was added to the residue
  5. filtrationThe precipitate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-337581ad1de44aa0b393aef07620f34c
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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