Dichloromethane → HCID 86711092, compound

HRID 1056573Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[CH2:23](Cl)[Cl:24]>O>[Cl:24][CH2:23][O:16][C:15](=[O:17])[CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid (1 g, 4.1 mmol) in DCM (25 mL) and H2O (25 mL) were added NaHCO3 (1.38 g, 16.4 mmol) and TBAHSO4 (0.14 g, 0.41 mmol). The reaction was stirred at 0° C. for 10 min, followed by the addition of a solution of chloromethyl sulfochloridate (499 μL, 5.5 mmol) in DCM (5 mL). The mixture was stirred at rt for 20 h, then washed with brine (25 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=10/1) to give the title compound as colorless oil (826 mg, 69.1%). The title compound was characterized by 1H NMR as shown below:

Workup

stirringThe mixture was stirred at rt for 20 h
washwashed with brine (25 mL)
dry with materialThe organic phase was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=10/1)

Sources & evidence

ORD record: ord-683ac8d4ae9c43c481c5b9091f202189
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399639B2

Reaction notes

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