Hydroxyamine hydrochloride → HCID 87709821, compound

HRID 1912746Notes

Reaction equation

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

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 86651522HCID 86651522, compound

Product 1

HCID 87709821HCID 87709821, compoundYield 40%

Procedure

Following the reaction conditions described in Example 1 and starting from 3β-(4-trifluoroacetamidobutylthio)androstane-6,17-dione and hydroxylamine hydrochloride, 3β-(4-trifluoroacetamidobutylthio)-6-(E)-hydroxyiminoandrostane-17-one (240 mg, 40%) was obtained. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.35 (1H, s), 9.40 (1H, t), 3.20 (4H, m), 2.55-0.90 (25H, m), 0.76 (3H, s), 0.67 (3H, s).

Workup

customthe reaction conditions

Sources & evidence

ORD record: ord-df27d1a0d31142df82d291a57e55e9d5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609644B2

Reaction notes

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