Hydrochloric Acid → Methyl 4-[3-(2-aminoethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl]pentanoate

HRID 1280865Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][O:14][CH:15]1[CH2:31][CH:30]2[C:18]([CH3:43])([CH:19]3[CH:27]([CH:28]([OH:32])[CH2:29]2)[CH:26]2[C:22]([CH3:41])([CH:23]([CH:33]([CH3:40])[CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:24][CH2:25]2)[CH:21]([OH:42])[CH2:20]3)[CH2:17][CH2:16]1.O.NN.Cl>CO>[NH2:3][CH2:12][CH2:13][O:14][CH:15]1[CH2:31][CH:30]2[C:18]([CH3:43])([CH:19]3[CH:27]([CH:28]([OH:32])[CH2:29]2)[CH:26]2[C:22]([CH3:41])([CH:23]([CH:33]([CH3:40])[CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:24][CH2:25]2)[CH:21]([OH:42])[CH2:20]3)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 40 °C

Procedure

1.7 g of methyl 4-{3-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethoxy]-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl}pentanoate and 0.52 ml of hydrazine hydrate (80%) are dissolved in 14 ml of methanol and the solution is refluxed for 3 hours. It is then cooled to 40° C. and the reaction mixture is treated with 8.7 ml of a 2N aqueous HCl solution. It is stirred at 40° C. for 30 minutes, then the volatile constituents are removed in vacuo. Chromatography on silica gel using acetone/water 10:1 yields 540 mg of resinous solid.

Workup

temperaturethe solution is refluxed for 3 hours
customthe volatile constituents are removed in vacuo

Sources & evidence

ORD record: ord-f81de7a0a9fa4e53b2be0c5035afb4af
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451781B1

Reaction notes

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