Acetic Anhydride → HCID 46852606, compound
Reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:8]2)=[O:6])[CH2:2]1.C(N(C(C)C)CC)(C)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>ClCCl>[C:27]([N:1]1[CH2:2][CH:3]([C:5]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:8]2)=[O:6])[CH2:4]1)(=[O:29])[CH3:28]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-(azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane (100 mg, 0.42 mmol) in dichloromethane (10 mL) cooled to 0° C. was added diisopropylethylamine (160 mg, 1.26 mmol) and acetic anhydride (45 mg, 0.51 mmol). The resulting mixture was stirred at RT for 3 h before it was quenched by addition of water (10 ml). The aqueous layer was extracted with dichloromethane (3×10 ml) and the combined organic layers were washed with saturated aqueous NaHCO3 (10 ml), dried (Na2SO4), filtered and concentrated. Purification by silica FCC (using a gradient of eluents; 100:0 to 99:1 DCM:2M NH3 in MeOH) followed by purification by preparative HPLC (Method 2) gave the title compound (35 mg, 30% yield) as colourless oil.
Workup
- customwas quenched by addition of water (10 ml)
- extractionThe aqueous layer was extracted with dichloromethane (3×10 ml)
- washthe combined organic layers were washed with saturated aqueous NaHCO3 (10 ml)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customPurification by silica FCC (
- custom100:0 to 99:1 DCM:2M NH3 in MeOH) followed by purification by preparative HPLC (Method 2)
Sources & evidence
- ORD record
- ord-4ba5f4f3c1464b31a88f1e0dbcc48af2
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912176B2
Reaction notes
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