Formaldehyde → 3,7,12-Triformyloxycholanoic acid chloride

HRID 2241844Notes

Reaction equation

C[C@@H]([C@@H]1[C@@]2(C)[C@@H](O)C[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4C[C@@H](O)[C@H]3[C@@H]2CC1)CCC(O)=O.C=O.[CH:32]([O:34][CH:35]1[CH2:58][CH2:57][C@@:56]2([CH3:59])[CH:37]([CH2:38][CH:39]([O:64][CH:65]=[O:66])[C@@H:40]3[C@@H:55]2[CH2:54][CH:53]([O:60][CH:61]=[O:62])[C@@:52]2([CH3:63])[C@H:41]3[CH2:42][CH2:43][C@@H:44]2[C@H:45]([CH3:51])[CH2:46][CH2:47][C:48](O)=[O:49])[CH2:36]1)=[O:33].C(Cl)(=O)C([Cl:70])=O>>[CH:32]([O:34][CH:35]1[CH2:58][CH2:57][C@@:56]2([CH3:59])[CH:37]([CH2:38][CH:39]([O:64][CH:65]=[O:66])[C@@H:40]3[C@@H:55]2[CH2:54][CH:53]([O:60][CH:61]=[O:62])[C@@:52]2([CH3:63])[C@H:41]3[CH2:42][CH2:43][C@@H:44]2[C@H:45]([CH3:51])[CH2:46][CH2:47][C:48]([Cl:70])=[O:49])[CH2:36]1)=[O:33]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 65578Oxalyl chloride

HCID 221493Cholic Acid

HCID 86628349HCID 86628349, compound

Product 1

HCID 874332713,7,12-Triformyloxycholanoic acid chloride

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.

Workup

customwas synthesized

Sources & evidence

ORD record: ord-51e728a84fe84d01ab2b2eb6a72be817
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07670751B2

Reaction notes

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