Reacción #3185

ord-78b65606c5ee45768c20fb14a7e7de91

Ecuación de reacción

CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)O)[C@@]4(C)CC[C@@H]32)C1
3β-acetoxy-5-cholenic acid
O=C(Cl)C(=O)Cl
oxalyl chloride
→
CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1
3β-acetoxy-5-cholenic acid chloride

Reactantes

CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)O)[C@@]4(C)CC[C@@H]32)C1
3β-acetoxy-5-cholenic acid
O=C(Cl)C(=O)Cl
oxalyl chloride

Reactivos

Ninguno

Disolventes

ClCCl
dichloromethane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 3β-acetoxy-5-cholenic acid (50.0 g, 118 mmole) in dry dichloromethane (200 ml) was added dropwise oxalyl chloride (30 ml, 448 mmole). The solution was stirred at room temperature for one hour and then concentrated in vacuo to obtain 3β-acetoxy-5-cholenic acid chloride 331. 1H NMR (400 MHz, CDCl3) δ: 0.70 (3H, s, 18-CH3), 0.95 (3H, d, 21-CH3), 1.05 (3H, s, 19-CH3), 2.04 (3H, s, --OCOCH3), 4.60 (1H, m, 3α-H), 5.38 (1H, m, 6-H). Compound 331 was used in the following step without purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05733899uspto-grants-1998_03