4-Methylmorpholine → HCID 22860040, compound

HRID 742074Notes

Reaction equation

HRID 742074 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-9ceb411dcf87429dbf3723d583333dc9
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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