4-Methylmorpholine → 1,1-Dimethylethyl [4-(methoxymethylamino)-4-oxobutyl]-carbamate

HRID 352140

Reaction equation

HRID 352140 reaction equation
Cl.CN[O:4][CH3:5].[CH3:6][N:7]1CCOCC1.Cl.CN(C)CCCN=C=NCC.[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=O)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:28][C:25]([O:29][C:30](=[O:31])[NH:32][CH2:33][CH2:34][CH2:35][C:36]([NH:7][CH2:6][O:4][CH3:5])=[O:38])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 871517791,1-Dimethylethyl [4-(methoxymethylamino)-4-oxobutyl]-carbamateYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(Dimethylamino)pyridine (6.11 g), N,O-dimethylhydroxylamine hydrochloride(4.88 g), N-methylmorpholine (5.06 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.58 g) were added in quick succession to a solution of 4-(tert-butoxycarbonylamino)butyric acid (10.16 g) in dichloromethane (200 ml). The reaction mixture was then stirred under ambient conditions for 18 h. The solution was then washed with 2M hydrochloric acid solution, 10% sodium bicarbonate solution and brine. The organic layer was separated, dried over magnesium sulfate, filtered and the filtrate evaporated to dryness to give the subtitle compound as a colourless oil (10.2 g, 83%).

Workup

  1. washThe solution was then washed with 2M hydrochloric acid solution, 10% sodium bicarbonate solution and brine
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-170e38e4aac64852af941fe35fecce62
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Linked notes

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