Triphenylphosphine → HCID 54295485, compound

HRID 486726Notes

Reaction equation

HRID 486726 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C.[C:32]([O:36][C:37]([C@@H:39]1[CH2:43][S:42][C@@H:41]([CH2:44]O)[CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[C:46]([OH:49])(=[S:48])[CH3:47]>C1COCC1>[C:46]([S:48][CH2:44][C@H:41]1[CH2:40][C@H:39]([C:37]([O:36][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:38])[CH2:43][S:42]1)(=[O:49])[CH3:47]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54267952HCID 54267952, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 54295485HCID 54295485, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of triphenylphosphine (391 mg) in THF (3 ml), azodicarboxylic acid diethylester (260 mg) dissolved in THF (1 ml) was added at -15°--10° C. under nitrogen atmosphere. To the mixture, trans-4-tert-butoxycarbonyl-2-hydroxymethyltetrahydrothiophene (compound No. 1-1, 150 mg) and thioacetic acid (114 mg) dissolved in THF (2 ml) were added at -20°--15° C., and the mixture was stirred for 1 hour at -20° C. and for 1 hour at room temperature. The mixture was concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 169 mg (82%) of the titled compound (compound No. 4-1).

Workup

  1. additionwas added at -15°--10° C. under nitrogen atmosphere
  2. additionwere added at -20°--15° C.
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-72410ae4e29f412b9bb724956c418a05
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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