Hydroxyamine hydrochloride → HCID 87709700, compound

HRID 1912655Notes

Reaction equation

C(O)(=O)/C=C/C(O)=O.[NH2:9][CH2:10][CH2:11][C:12]([O:14][C@H:15]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[CH:17]([C:18](=O)[CH2:19][C@@H:20]3[C@@H:29]2[CH2:28][CH2:27][C@@:25]2([CH3:26])[C@H:21]3[CH2:22][CH2:23][C:24]2=[O:34])[CH2:16]1)=[O:13].[ClH:36].[NH2:37][OH:38]>>[ClH:36].[NH2:9][CH2:10][CH2:11][C:12]([O:14][C@H:15]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[CH:17](/[C:18](=[N:37]/[OH:38])/[CH2:19][C@@H:20]3[C@@H:29]2[CH2:28][CH2:27][C@@:25]2([CH3:26])[C@H:21]3[CH2:22][CH2:23][C:24]2=[O:34])[CH2:16]1)=[O:13]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 69134025HCID 69134025, compound

Product 1

HCID 87709700HCID 87709700, compound

Procedure

Following the procedure described in Example 1 and starting from 3β-(3-aminopropionyloxy)androstane-6,17-dione fumarate (Prepn. 69, 260 mg) and hydroxylamine hydrochloride (41 mg), the title compound I-dm was obtained (168 mg, 75%), after purification by flash chromatography (SiO2; CH2Cl2:MeOH 9:1). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.42 (1H, s), 8.13 (3H, bb), 4.63 (1H, m), 3.27 (1H, m), 2.98 (2H, t), 2.64 (2H, t), 2.45-0.95 (19H, m), 0.77 (3H, s), 0.69 (3H, s).

Sources & evidence

ORD record: ord-f5e7ab85bb6c4c6b93aded095b374cff
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609644B2

Reaction notes

Loading…