4-Methylmorpholine → (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate

HRID 431406

Reaction equation

HRID 431406 reaction equation
Cl.C(N=C=NCCCN(C)C)C.C1([NH2+]C2CCCCC2)CCCCC1.[C:26]([NH:33][C@H:34]([C:38]([O-:40])=O)[CH2:35][CH2:36][CH3:37])([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].Cl.[CH3:42][NH:43][O:44][CH3:45].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH3:42][N:43]([O:44][CH3:45])[C:38](=[O:40])[C@H:34]([CH2:35][CH2:36][CH3:37])[NH:33][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 131720340n-Boc-l-norvaline dicyclohexylammonium salt

Product 1

HCID 9992774(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamateYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (443 mg) in one portion was added to a mixture of N-Boc-L-norvaline dicyclohexylammonium salt (838 mg), N,O-dimethylhydroxylamine hydrochloride (215 mg), 1-hydroxybenzotriazole monohydrate (340 mg), and N-methylmorpholine (0.28 ml) in dimethyl formamide (DMF, 20 ml) at 0° C. The mixture was stirred at 0° C. for 2 hours, then at room temperature for 40 hours. The reaction was quenched with water (80 mL) and the mixture was extracted with ethyl acetate (EtOAc, 3×100 mL). The combined organic layers were washed with aqueous 10% hydrogen chloride (HCl), saturated sodium bicarbonate (NaHCO3), and brine, then dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated to afford the product (546 mg) as an oil.

Workup

  1. waitat room temperature for 40 hours
  2. customThe reaction was quenched with water (80 mL)
  3. extractionthe mixture was extracted with ethyl acetate (EtOAc, 3×100 mL)
  4. washThe combined organic layers were washed with aqueous 10% hydrogen chloride (HCl), saturated sodium bicarbonate (NaHCO3), and brine
  5. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8c0bdf35f724418eb0deac8ada8c2e76
Source dataset
uspto-grants-2003_12
Patent number
US06660268B1

Linked notes

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