Hydroxyamine hydrochloride → HCID 87709668, compound

HRID 1912751Notes

Reaction equation

[C:1]([N:11]([CH3:38])[CH2:12][CH2:13][C:14]([O:16][C@H:17]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[CH:19]([C:20](=O)[CH2:21][C@@H:22]3[C@@H:31]2[CH2:30][CH2:29][C@@:27]2([CH3:28])[C@H:23]3[CH2:24][CH2:25][C:26]2=[O:36])[CH2:18]1)=[O:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[NH2:40][OH:41]>>[C:1]([N:11]([CH2:12][CH2:13][C:14]([O:16][C@H:17]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[CH:19](/[C:20](=[N:40]/[OH:41])/[CH2:21][C@@H:22]3[C@@H:31]2[CH2:30][CH2:29][C@@:27]2([CH3:28])[C@H:23]3[CH2:24][CH2:25][C:26]2=[O:36])[CH2:18]1)=[O:15])[CH3:38])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 69133363HCID 69133363, compound

Product 1

HCID 87709668HCID 87709668, compoundYield 60%

Procedure

The procedure described in Prepn. 20 was followed starting from 3β-(N-carbobenzyloxy-N-methyl-3-aminopropionyloxy)androstane-6,17-dione (0.70 g) and hydroxylamine hydrochloride. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 60/40) to give the title compound (0.43 g, 60%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.31 (1H, s), 7.30 (5H, m), 5.05 (2H, s), 4.56 (1H, m), 3.50-0.87 (27H, m), 0.78 (3H, s), 0.68 (3H, s).

Workup

customThe residue was purified by flash chromatography (SiO2, n-hexane/acetone 60/40)

Sources & evidence

ORD record: ord-76cacbf2fb8b44ceb79fc1cabaabf7d0
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609644B2

Reaction notes

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