4-Methylmorpholine → HCID 178459247, compound

HRID 964708Notes

Reaction equation

HRID 964708 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[C@H:14]([C@H:18]2[CH2:23][CH2:22][C@H:21]([O:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]2)[C:15]([OH:17])=O)(=[O:12])=[O:11])=[CH:6][CH:5]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[C:53]([O:57][NH2:58])([CH3:56])([CH3:55])[CH3:54].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl.O>[C:53]([O:57][NH:58][C:15](=[O:17])[C@H:14]([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])[CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[C@H:18]1[CH2:23][CH2:22][C@H:21]([O:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]1)([CH3:56])([CH3:55])[CH3:54]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 178459249HCID 178459249, compound

Product 1

HCID 178459247HCID 178459247, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-(trans-4-propoxycyclohexyl) acetic acid hydrochloride (2.65 g, 4.82 mmol), 1-hydroxybenzotriazole (0.65 g, 4.81 mmol), 4-methylmorpholine (2.93 mL, 26.5 mmol), and O-t-butylhydroxylamine hydrochloride (1.81 g, 14.4 mmol) are dissolved in methylene chloride (100 mL). N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (1.1 g, 5.8 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% methanoilmethylene chloride) to give N-(t-butyloxy)-2(R)-[(4-methoxybenzenesulfonyl)-(4-picolyl)amino]-2-(trans-4-propoxy-cyclohexyl)-acetamide.

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% methanoilmethylene chloride)

Sources & evidence

ORD record
ord-c189d63580f347499b0e1f2dd2f7ef17
Source dataset
uspto-grants-1998_06
Patent number
US05770624

Reaction notes

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