Hydrochloric Acid → HCID 88116399, compound

HRID 2301757Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][N:12]([CH:22]1[CH2:26][CH:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]([CH2:33][OH:34])[CH2:23]1)[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl>[CH3:11][N:12]([CH:22]1[CH2:26][CH:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]([CH:33]=[O:34])[CH2:23]1)[S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:14])=[O:15]

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of oxalyl chloride (0.045 mL, 0.50 mmol) in methylene chloride (2 mL) at −70° C. was added dropwise DMSO (0.045 mL, 1.0 mmol). After 15 min, a solution of 1-(RS)-(N-(methyl)-N-(phenylsulfonyl)amino)-3-(SR)-(hydroxymethyl)-4-(SR)-phenylcyclopentane (Higher Rf isomer from Step C) (65 mg, 0.2 mmol) in methylene chloride (2 mL) was added. The reaction was stirred at −70° C. for 1.5 h and then DIPEA (0.35 mL, 2.0 mmol) was added. After a further 10 min, the mixture was allowed to warm to RT for 1 h and was then diluted with methylene chloride and poured into dilute aq. HCl and the layers were separated. The aq. layer was reextracted with a second portion of methylene chloride and the organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo. The residue was purified by FC using a gradient of 20 to 30% ethyl acetate in hexanes to give the title product (57 mg) as an oil.

Workup

waitAfter a further 10 min
temperatureto warm to RT for 1 h
customthe layers were separated
washeach washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by FC

Sources & evidence

ORD record: ord-3d7caad4a7534b969791ffb450836959
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500844B1

Reaction notes

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