4-Methylmorpholine → HCID 23298253, compound

HRID 1953464Notes

Reaction equation

HRID 1953464 reaction equation
CN1CCOCC1.Cl[S:9]([C:12]1[CH:17]=[CH:16][N:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14](=[O:24])[C:13]=1[N:25](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)(=[O:11])=[O:10].Cl.[CH:41]1([CH2:45][NH2:46])[CH2:44][CH2:43][CH2:42]1>C(Cl)Cl>[NH2:25][C:13]1[C:14](=[O:24])[N:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[CH:17][C:12]=1[S:9](=[O:10])(=[O:11])[NH:46][CH2:45][CH:41]1[CH2:44][CH2:43][CH2:42]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 217079441-Cyclobutylmethanamine hydrochlorideHCID 232982504-Chlorosulfonyl-3-(N,N-di-t-butoxycarbonylamino)-1-ethyloxycarbonylmethyl-2-pyridinone

Product 1

HCID 23298253HCID 23298253, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

NMM (1.43 mL, 13.0 mmol) was added to a stirred mixture of 4-chlorosulfonyl-3-(N,N-di-t-butoxycarbonylamino)-1-ethyloxycarbonylmethyl-2-pyridinone (as a mixture from Step H, 0.84 g) and cyclobutylmethylamine hydrochloride (348 mg, 2.86 mmol) in methylene chloride (15 mL). After 16 h the reaction was diluted with methylene chloride and washed with 10% citric acid solution. The organic layer was dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography on silica (40% ethyl acetate/hexanes). HCl gas was bubbled through a stirred solution of the resulting compound in ethyl acetate (10 mL) at 0° C. for 15 min. The reaction was warmed to rt and after a further 3 h it was evaporated to give the title compound as a solid;

Workup

  1. washwashed with 10% citric acid solution
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by flash column chromatography on silica (40% ethyl acetate/hexanes)
  5. customHCl gas was bubbled through a stirred solution of the resulting compound in ethyl acetate (10 mL) at 0° C. for 15 min
  6. customwas evaporated

Sources & evidence

ORD record
ord-c9880aa6f3674fa69b86f03a7c17fc6d
Source dataset
uspto-grants-2000_09
Patent number
US06117888

Reaction notes

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