1,2-Dichloroethane → HCID 22458230, compound

HRID 2185565Notes

Reaction equation

HRID 2185565 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].CCN(C(C)C)C(C)C.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][C:30]([OH:32])=O)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(Cl)CCl>O1CCOCC1.CN(C)C1C=CN=CC=1>[CH3:5][O:4][N:3]([CH3:2])[C:30](=[O:32])[CH2:29][CH2:28][CH:25]1[CH2:24][CH2:23][N:22]([C:20]([O:19][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:21])[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

Product 1

HCID 22458230HCID 22458230, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Procedure

Molecular sieve pellets (4 Å), N,O-dimethylhydroxylamine hydrochloride (227 mg, 3.32 mmol), and DIEA (0.41 mL, 0.30 g, 2.4 mmol) were added to a solution of 3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionic acid (500 mg, 1.94 mmol, from Step A) in 1,4-dioxane (10 mL). 4-(Dimethylamino)pyridine (57 mg, 0.47 mmol) and EDC (483 mg, 2.52 mmol) were added and the mixture was stirred for 16 h at rt. The mixture was partitioned between EtOAc (50 mL) and 1 N aq. HCl (50 mL). The aqueous layer was extracted with EtOAc (50 mL). The organic layers were washed with sat'd NaCl (30 mL), dried (Na2SO4), decanted, and evaporated to give 583 mg of N-methoxy-N-methyl-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionamide.

Workup

  1. customThe mixture was partitioned between EtOAc (50 mL) and 1 N aq. HCl (50 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  3. washThe organic layers were washed with sat'd NaCl (30 mL)
  4. dry with materialdried (Na2SO4)
  5. customdecanted
  6. customevaporated

Sources & evidence

ORD record
ord-ee70506db4724046ae86d0d00b269366
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

Loading…