4-Methylmorpholine → HCID 22860040, compound

HRID 1720633Notes

Reaction equation

HRID 1720633 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[C@@H]2CCCCC2CC(O)=O)(=[O:12])=[O:11])=[CH:6][CH:5]=1.ON1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.CN1CC[O:45][CH2:44][CH2:43]1.Cl.[C:49]([O:53][NH2:54])([CH3:52])([CH3:51])[CH3:50].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl.O>[C:49]([O:53][NH:54][C:44](=[O:45])[C@H:43]([N:13]([S:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)(=[O:11])=[O:12])[CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)([CH3:52])([CH3:51])[CH3:50]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 70060392HCID 70060392, compound

Product 1

HCID 22860040HCID 22860040, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2(R)-[[4-Methoxybenzenesulfonyl](4-picolyl)amino]-cyclohexylacetic acid hydrochloride (1.8 g, 4.2 mmol), 1-hydroxybenzotriazole (0.65 g, 4.81 mmol), 4-methyl-morpholine (2.4 mL, 24.04 mmol), and O-t-butylhydroxylamine hydrochloride (1.81 g, 14.4 mmol) are dissolved in methylene chloride (100 mL). N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (1.2 g, 6.25 mmol) is added, and the reaction is stirred overnight. The reaction is then diluted with water and extracted with methylene chloride. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (5% methanol/methylene chloride) to give N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]-(4-picolyl)amino]-2-cyclohexylacetamide.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe crude product is purified by silica gel chromatography (5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-2a7c2386111b4f98b0f1e016ee5fbdfc
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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