Hydroxyamine hydrochloride → HCID 87709822, compound

HRID 1912745Notes

Reaction equation

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

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 86651520HCID 86651520, compound

Product 1

HCID 87709822HCID 87709822, compoundYield 50%

Procedure

Following the procedure described in Example 1 and starting from 3β-(3-trifluoroacetamidopropylthio)androstane-6,17-dione (395 mg) and hydroxylamine hydrochloride (65 mg), 3β-(3-trifluoroacetamidopropylthio)-6-(E)-hydroxyiminoandrostane-17-one (200 mg, 50%) was obtained. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.40 (1H, s), 9.42 (1H, t), 3.23 (4H, m), 2.55-0.90 (23H, m), 0.76 (3H, s), 0.67 (3H, s).

Sources & evidence

ORD record: ord-9b3d7548004f4b94a24167df6319ad20
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609644B2

Reaction notes

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