Potassium Carbonate → HCID 15068026, compound

HRID 1031929Notes

Reaction equation

HRID 1031929 reaction equation
[C:1]([O:12][CH:13]1[CH2:17][CH2:16][C:15]2([CH2:22][C:21](=[O:23])[N:20]([CH2:24][CH2:25][CH2:26][CH2:27]Br)[C:19](=[O:29])[CH2:18]2)[CH2:14]1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH:30]1[CH:31]=[CH:32][C:33]2[S:38][N:37]=[C:36]([N:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)[C:34]=2[CH:35]=1.C([O-])([O-])=O.[K+].[K+].CO.C(Cl)Cl>CC#N>[C:1]([O:12][CH:13]1[CH2:17][CH2:16][C:15]2([CH2:22][C:21](=[O:23])[N:20]([CH2:24][CH2:25][CH2:26][CH2:27][N:42]3[CH2:43][CH2:44][N:39]([C:36]4[C:34]5[CH:35]=[CH:30][CH:31]=[CH:32][C:33]=5[S:38][N:37]=4)[CH2:40][CH2:41]3)[C:19](=[O:29])[CH2:18]2)[CH2:14]1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 21226129Dichloromethane methanolHCID 22167009HCID 22167009, compound

Product 1

HCID 15068026HCID 15068026, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-(4-Bromobutyl)-7,9-dioxo-8-azaspiro[4.5]decan-2-yl decanoate (3.03 g, 1.00 equiv), BITP 14 (2.38 g, 1.69 equiv) and K2CO3 (3.37 g, 3.80 equiv) were reacted in 125 mL of CH3CN according to the general procedure. Flash chromatography with a 3% to 5% MeOH/CH2Cl2 gradient yielded 12 (2.02 g, 52%) as a yellow oil. Conversion to the oxalate salt and recrystallization from CH3CN/EtOH afforded the analytically pure test compound, m.p. 117-9° C.

Sources & evidence

ORD record
ord-26a0de72ab654c65a92db8dfd391e337
Source dataset
uspto-grants-1990_09
Patent number
US04956368

Reaction notes

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