Tert-Butylamine → HCID 66816838, compound
Reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.FC(F)(F)C(O)=O.[Cl:32][C:33]1[CH:34]=[C:35]([S:39]([N:42]2[CH2:58][CH2:57][C:45]3([N:49]=[C:48]([CH:50]4[CH2:55][CH2:54][CH2:53][NH:52][CH2:51]4)[NH:47][C:46]3=[O:56])[CH2:44][CH2:43]2)(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=1>C(Cl)Cl>[C:13]([NH:17][C:2]([N:52]1[CH2:53][CH2:54][CH2:55][CH:50]([C:48]2[NH:47][C:46](=[O:56])[C:45]3([CH2:57][CH2:58][N:42]([S:39]([C:35]4[CH:36]=[CH:37][CH:38]=[C:33]([Cl:32])[CH:34]=4)(=[O:41])=[O:40])[CH2:43][CH2:44]3)[N:49]=2)[CH2:51]1)=[O:4])([CH3:16])([CH3:15])[CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of triphosgene (345 mg, 1.16 mmol) in CH2Cl2 (7 ml) was added to a solution of tert-butylamine (331 μl, 3.14 mmol) and triethylamine (876 μl, 6.29 mmol) in CH2Cl2 (10 ml) at −78° C. The mixture was stirred at room temperature for 10 minutes, followed by addition of a solution of 8-(3-chloro-benzenesulfonyl)-2-piperidin-3-yl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one trifluoroacetate (165 mg, 0.314 mmol) and triethylamine (876 μl, 6.29 mmol) in CH2Cl2 (2 ml). Further, the reaction mixture was stirred at room temperature for 10 minutes and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3-[8-(3-Chloro-benzenesulfonyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-en-2-yl]-piperidine-1-carboxylic acid tert-butylamide as a colorless oil (40 mg, yield 25%).
Workup
- stirringFurther, the reaction mixture was stirred at room temperature for 10 minutes
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-921cf40310704b68be934d9700085cbd
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169254B2
Reaction notes
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