Reaction #2329026

ord-51e728a84fe84d01ab2b2eb6a72be817

Reaction equation

O=C(Cl)C(=O)Cl
oxalyl chloride
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
cholic acid
C=O
formalin
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(OC=O)CC4CC(OC=O)CC[C@]4(C)[C@H]3CC(OC=O)[C@]12C
3,7,12-triformyloxycholanoic acid
→
C[C@H](CCC(=O)Cl)[C@H]1CC[C@H]2[C@@H]3C(OC=O)CC4CC(OC=O)CC[C@]4(C)[C@H]3CC(OC=O)[C@]12C
crude product
C[C@H](CCC(=O)Cl)[C@H]1CC[C@H]2[C@@H]3C(OC=O)CC4CC(OC=O)CC[C@]4(C)[C@H]3CC(OC=O)[C@]12C
3,7,12-triformyloxycholanoic acid chloride

Reactants

O=C(Cl)C(=O)Cl
oxalyl chloride
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
cholic acid
C=O
formalin
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(OC=O)CC4CC(OC=O)CC[C@]4(C)[C@H]3CC(OC=O)[C@]12C
3,7,12-triformyloxycholanoic acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherwas synthesized

Procedure

By a standard technique using cholic acid and formalin, 3,7,12-triformyloxycholanoic acid was synthesized. It was then chlorinated using oxalyl chloride. The crude product thus obtained was used in the subsequent step of esterification without purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07670751B2uspto-grants-2010_03