Dimethylformamide → HCID 59271750, compound

HRID 1186048Notes

Reaction equation

C(O[C:5]1([C:26](=[O:29])[CH2:27]O)[C@:21]2([CH3:22])[CH:8]([CH:9]3[C:18](=[CH:19][CH2:20]2)[C@:17]2([CH3:23])[C:12](=[CH:13][C:14](=[O:24])[CH:15]=[CH:16]2)[C@@H:11]([CH3:25])[CH2:10]3)[CH2:7][CH2:6]1)(=O)C.[C:30](=[O:33])([O-])[O-:31].[CH3:34]N(C)C=O>>[C:30]([O:31][CH2:27][C:26](=[O:29])[C:5]1[C@:21]2([CH3:22])[CH:8]([CH:9]3[C:18](=[CH:19][CH2:20]2)[C@:17]2([CH3:23])[C:12](=[CH:13][C:14](=[O:24])[CH:15]=[CH:16]2)[C@@H:11]([CH3:25])[CH2:10]3)[CH2:7][CH:6]=1)(=[O:33])[CH3:34]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 19660Carbonate Ion

HCID 67283722HCID 67283722, compound

Product 1

HCID 59271750HCID 59271750, compound

Procedure

(6S,10R,13S)-17-(2-hydroxyacetyl)-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl acetate is heated with 2 equivalents of postassium carbonate in dimethyl formamide. Standard aqueous workup yields the title compound.

Sources & evidence

ORD record: ord-01bacf0c1f494160912383320f3c9cac
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673887B2

Reaction notes

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