Water → Ethanethioic acid cis-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

HRID 54764

Reaction equation

HRID 54764 reaction equation
[OH:1][CH2:2][C@H:3]1[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1.O.ClC(Cl)(Cl)[C:15]([N:17]=C=O)=[O:16]>C(Cl)Cl.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[NH2:17][C:15]([O:1][CH2:2][C@H:3]1[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1)=[O:16]

Participants

8

Reactant 3

HCID 962WaterHCID 76400Trichloroacetyl isocyanateHCID 86750314Ethanethioic acid cis (+/-)-S-[tetrahydro-5-(hydroxymethyl)-3-furanyl]ester

Product 1

HCID 86750313Ethanethioic acid cis-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

The title compound is prepared by the procedure of Example 7 using 0.28 g of product from Example 9 in 20 ml of methylene chloride, 0.208 ml of trichloroacetyl isocyanate, 0.80 ml of acetic acid, 6.79 ml of 1M tetrabutylammonium fluoride in tetrahydrofuran and 0.37 ml of water to give 0.320 g of the desired product.

Sources & evidence

ORD record
ord-5ce210a07f8045098a967abf4013a763
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Linked notes

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