Acetic Anhydride → Ethanethioic acid trans-(+/-)-S-[5-[[Acetyl(phenylmethoxy)amino]methyl]tetrahydro-3-furanyl]ester

HRID 1290379Notes

Reaction equation

HRID 1290379 reaction equation
[C:1]1([CH2:7][O:8][N:9]([CH2:18][C@@H:19]2[O:23][CH2:22][C@@H:21]([S:24][C:25](=[O:27])[CH3:26])[CH2:20]2)[C:10](OCC(Cl)(Cl)Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28](OC(=O)C)(=O)C>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[C:10]([N:9]([CH2:18][C@@H:19]1[O:23][CH2:22][C@@H:21]([S:24][C:25](=[O:27])[CH3:26])[CH2:20]1)[O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:11])[CH3:28]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 86752473Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-[[(phenylmethoxy)[(2,2,2-trichloroethoxy)carbonyl]amino]methyl]-3-furanyl] ester

Product 1

HCID 86750754Ethanethioic acid trans-(+/-)-S-[5-[[Acetyl(phenylmethoxy)amino]methyl]tetrahydro-3-furanyl]ester

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature solution, under argon, of 0.188 g of product from Example 71 in 2.3 ml of glacial acetic acid is added 0.269 g of zinc dust. The reaction is stirred 10 minutes and 155 microliter of acetic anhydride is added. The reaction is stirred at room temperature overnight, diluted with ethyl acetate and filtered. The filtrate is concentrated in vacuo to give 0.110 g of the desired product.

Workup

  1. stirringThe reaction is stirred at room temperature overnight
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f1f04a93c9ea469b846a3df3053b659a
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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