Ammonium Chloride → HCID 66818552, compound

HRID 1755070Notes

Reaction equation

HRID 1755070 reaction equation
C([Li])CCC.[C:6]([O:10][C:11](=[O:40])[N:12]([C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([S:26]([N:29]2[CH2:38][CH2:37][C:32]3([O:36][CH2:35][CH2:34][O:33]3)[CH2:31][CH2:30]2)(=[O:28])=[O:27])[CH2:23][CH2:24]Cl)=[C:16]([CH3:39])[CH:15]=1)[CH3:13])([CH3:9])([CH3:8])[CH3:7].[Cl-].[NH4+]>C1COCC1>[C:6]([O:10][C:11](=[O:40])[N:12]([C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][C:22]2([S:26]([N:29]3[CH2:38][CH2:37][C:32]4([O:36][CH2:35][CH2:34][O:33]4)[CH2:31][CH2:30]3)(=[O:28])=[O:27])[CH2:24][CH2:23]2)=[C:16]([CH3:39])[CH:15]=1)[CH3:13])([CH3:9])([CH3:8])[CH3:7].[O:33]1[C:32]2([CH2:31][CH2:30][N:29]([S:26]([C:22]3([CH2:21][C:17]4[C:18]([CH3:20])=[CH:19][C:14]([NH:12][CH3:13])=[CH:15][C:16]=4[CH3:39])[CH2:23][CH2:24]3)(=[O:27])=[O:28])[CH2:38][CH2:37]2)[O:36][CH2:35][CH2:34]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 66817946HCID 66817946, compoundHCID 178418339Butyllithium

Product 2

HCID 66818552HCID 66818552, compoundHCID 66818604HCID 66818604, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (1.6 M solution in hexane, 345 μl, 0.552 mmol) was added to a solution of {4-[4-chloro-2-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-butyl]-3,5-dimethyl-phenyl}-methyl-carbamic acid tert-butyl ester (115.0 mg, 0.2165 mmol) in THF (3.0 ml) at −78° C. over three minutes. The mixture was stirred at the same temperature for five minutes, and then warmed and further stirred at room temperature for one hour. A 50% saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give {4-[1-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-cyclopropylmethyl]-3,5-dimethyl-phenyl}-methyl-carbamic acid tert-butyl ester and {4-[1-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-cyclopropylmethyl]-3,5-dimethyl-phenyl}-methyl-amine as a mixture (46.0 mg, 43% and 19.6 mg, 23%). This was used in the next reaction without complete purification.

Workup

  1. temperaturewarmed
  2. stirringfurther stirred at room temperature for one hour
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was then dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-28c6e816099a479fb0c8d4039cb55d08
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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