Hydrochloric Acid → HCID 70586608, compound

HRID 1701432Notes

Reaction equation

[CH2:1]([N:3]([CH2:6][C:7]([O:9][C@H:10]1[CH2:29][C@@:28]2([CH3:30])[C@@H:21]([CH2:22][CH2:23][C@@H:24]2[C:25](=[O:27])[CH3:26])[C@H:20]2[C@H:11]1[C@:12]1([CH3:32])[C@@H:17]([CH2:18][CH2:19]2)[CH2:16][C@@H:15]2[O:31][C@@H:14]2[CH2:13]1)=[O:8])[CH2:4][CH3:5])[CH3:2].C(=O)(O)[O-].[Na+].[ClH:38]>>[Cl:38][C@H:14]1[CH2:13][C@@:12]2([CH3:32])[C@@H:17]([CH2:18][CH2:19][C@@H:20]3[C@@H:11]2[C@@H:10]([O:9][C:7](=[O:8])[CH2:6][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:29][C@@:28]2([CH3:30])[C@H:21]3[CH2:22][CH2:23][C@@H:24]2[C:25](=[O:27])[CH3:26])[CH2:16][C@@H:15]1[OH:31]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 516892Sodium Bicarbonate

HCID 86736865HCID 86736865, compound

Product 1

HCID 70586608HCID 70586608, compound

Procedure

A solution of 11β-diethylaminoacetoxy-2α,3α-epoxy-5α-pregnan-20-one (800 mg) in concentrated hydrochloric acid (6 ml) was kept at room temperature for 15 minutes and then diluted with a large excess of sodium bicarbonate solution. The precipitated solid (767 mg) was collected by filtration and purified by preparative TLC (ethylacetate) and crystallization from petroleum ether to afford title compound, (305 mg). m.p. 182°-187°, [α]D +101.4°.

Workup

filtrationThe precipitated solid (767 mg) was collected by filtration
custompurified by preparative TLC (ethylacetate) and crystallization from petroleum ether

Sources & evidence

ORD record: ord-ae6abe34969c4e7792e8039023327b8c
Source dataset: uspto-grants-1980_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04192871

Reaction notes

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