Reaktion #83042

ord-5ce210a07f8045098a967abf4013a763

Reaktionsgleichung

CC(=O)S[C@@H]1CO[C@H](CO)C1
product
CC(=O)S[C@@H]1CO[C@H](CO)C1
Ethanethioic acid cis(+/-)-S-[tetrahydro-5-(hydroxymethyl)-3-furanyl]ester
O=C=NC(=O)C(Cl)(Cl)Cl
trichloroacetyl isocyanate
O
water
→
CC(=O)S[C@@H]1CO[C@H](COC(N)=O)C1
desired product
CC(=O)S[C@@H]1CO[C@H](COC(N)=O)C1
Ethanethioic acid cis-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

Edukte

CC(=O)S[C@@H]1CO[C@H](CO)C1
product
CC(=O)S[C@@H]1CO[C@H](CO)C1
Ethanethioic acid cis(+/-)-S-[tetrahydro-5-(hydroxymethyl)-3-furanyl]ester
O=C=NC(=O)C(Cl)(Cl)Cl
trichloroacetyl isocyanate
O
water

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride
CC(=O)O
acetic acid
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetrabutylammonium fluoride
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05623081uspto-grants-1997_04