Triphenylphosphine → Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-[[(phenylmethoxy)[(2,2,2-trichloroethoxy)carbonyl]amino]methyl]-3-furanyl] ester

HRID 1290378Notes

Reaction equation

HRID 1290378 reaction equation
O[CH2:2][C@@H:3]1[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1.[Cl:12][C:13]([Cl:28])([Cl:27])[CH2:14][O:15][C:16](=[O:26])[NH:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:20]1([CH2:19][O:18][N:17]([CH2:2][C@@H:3]2[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]2)[C:16]([O:15][CH2:14][C:13]([Cl:12])([Cl:27])[Cl:28])=[O:26])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11098567(Phenylmethoxy)carbamic acid 2,2,2-trichloroethyl esterHCID 15346553Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-(hydroxymethyl)-3-furanyl]ester

Product 1

HCID 86752473Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-[[(phenylmethoxy)[(2,2,2-trichloroethoxy)carbonyl]amino]methyl]-3-furanyl] esterYield 200.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution, under argon, of 1.0 g of product from Example 6, 1.69 g of product from Example 70, 1.49 g of triphenylphosphine and 5.4 ml of tetrahydrofuran is added 0.988 g of diethyl azodicarboxylate in 1.4 ml of tetrahydrofuran. The reaction is stirred at room temperature for 48 hours, filtered and the filtrate concentrated in vacuo to give 5.18 g of thick oil. The oil is purified by chromatography (Silica Gel: 15-25% ethyl acetate/hexane) to give 0.805 g of the desired product.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-70e6722cf6684f6ea0871533a0ffa7ed
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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