Pyridine → HCID 101603487, compound

HRID 1870474Notes

Reaction equation

[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:16](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:17][CH2:18][OH:19])=[CH:11][CH:10]=1)[CH2:4][CH3:5].N1C=CC=CC=1.[S:38](Cl)([C:41]1[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=1)(=[O:40])=[O:39]>C(Cl)Cl>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:16](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:17][CH2:18][O:19][S:38]([C:41]2[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=2)(=[O:40])=[O:39])=[CH:11][CH:10]=1)[CH2:4][CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Cis- or trans- N,N-diethylhydroxytamoxifen (II) (100 mg, 0.27 mmol) was dissolved in methylene chloride (2 ml) and cooled to 0° C. Pyridine (150 μl) and tosyl chloride (55 mg, 0.27 mmol) were added. After 2 hours, the reaction mixture was diluted with methylene chloride and washed with water. The methylene chloride layer was evaporated and chromatographed on a 18C column using 85:15:1 acetonitrile/water/triethylamine as eluant to yield cis (51 mg, 34%, oil) or trans tosyl analog (30 mg, 20%, oil): m/z 569(60, M+), 397(20, +OSO2PhCH3). Values for aliphatic protons are presented in Table 2.

Workup

washwashed with water
customThe methylene chloride layer was evaporated
customchromatographed on a 18C column
customto yield cis (51 mg, 34%, oil) or trans tosyl analog (30 mg, 20%, oil)

Sources & evidence

ORD record: ord-7ae97f0cdfbb4d22bc88d5f8c8972b06
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06096874

Reaction notes

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