tert-Butyl methyl ether → HCID 68922468, compound

HRID 1191293Notes

Reaction equation

HRID 1191293 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH:21]4[CH2:26][CH2:25]S[CH2:23][CH2:22]4)[CH:16]3[CH2:27][CH2:28][NH:29][C:30]([CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)=[O:31])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=O)C=1.[S:56]([O-:60])([O-])(=[O:58])=S.[Na+].[Na+].C(OC)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH:21]4[CH2:26][CH2:25][S:56](=[O:60])(=[O:58])[CH2:23][CH2:22]4)[CH:16]3[CH2:27][CH2:28][NH:29][C:30]([CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[CH2:34][CH2:33]3)=[O:31])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 68918566HCID 68918566, compound

Product 1

HCID 68922468HCID 68922468, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl 4-[({2-[(2RS,3SR)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1-(tetrahydro-2H-thiopyran-4-yl)piperidin-2-yl]ethyl}amino)carbonyl]piperidine-1-carboxylate (73.5 mg) in dichloromethane (1.5 mL), trifluoroacetic acid (17 μL) and m-chloroperbenzoic acid (40 mg) were added and then stirred at room temperature for 3 hours. The reaction solution was added aqueous sodium thiosulfate solution and excessive tert-butylmethyl ether, extracted with aqueous 2N sodium hydroxide solution and saturated brine and obtained a crude product of the title compound (84 mg). The obtained crude product was purified by silica gel column chromatography (ethyl acetate:methanol:28% aqueous ammonia=1000:10:1→80:20:2) to obtain a more polar compound and a less polar compound of the title compound having the following physical properties.

Workup

  1. extractionextracted with aqueous 2N sodium hydroxide solution and saturated brine

Sources & evidence

ORD record
ord-1c4f277b406b49939183cc2eded60dc4
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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