4-Methylmorpholine → tert-Butyl {2-[(methoxymethyl)amino]-2-oxoethyl}carbamate

HRID 1354401Notes

Reaction equation

HRID 1354401 reaction equation
Cl.CN[O:4][CH3:5].CCN=C=NCCC[N:14]([CH3:16])C.CN1CCOCC1.[CH3:24][C:25]([CH3:35])([O:27][C:28]([NH:30][CH2:31][C:32]([OH:34])=O)=[O:29])[CH3:26]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:5][O:4][CH2:16][NH:14][C:32](=[O:34])[CH2:31][NH:30][C:28](=[O:29])[O:27][C:25]([CH3:24])([CH3:26])[CH3:35]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 21105795tert-Butyl {2-[(methoxymethyl)amino]-2-oxoethyl}carbamateYield 78.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

N,O-Dimethylhydroxylamine hydrochloride (1.95 g), EDCI (3.83 g), N-methylmorpholine (2.2 ml) and DMAP (2.44 g) were added to a solution of N-[(1,1-dimethylethoxy)carbonyl]glycine (3.5 g) in dichloromethane (60 ml) and then stirred at room temperature for 3 days. Dichloromethane (100 ml) was added and then the solution was washed with 2M hydrochloric acid (three times), NaHCO3 solution (three times) and water (three times) and then dried (MgSO4). The organic layer was separated and the aqueous layer was further extracted twice. The solvent was evaporated to give the sub-title compound (3.42 g).

Workup

  1. washthe solution was washed with 2M hydrochloric acid (three times), NaHCO3 solution (three times) and water (three times)
  2. dry with materialdried (MgSO4)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted twice
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4529cbab47294f1caf831523f994f3be
Source dataset
uspto-grants-2007_05
Patent number
US07223794B2

Reaction notes

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