4-Methylmorpholine → HCID 86586791, compound

HRID 2121215Notes

Reaction equation

HRID 2121215 reaction equation
C(OC([NH:8][C@H:9]([C:14](O)=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=O)(C)(C)C.CN1CC[O:21][CH2:20]C1.ClC(O[CH2:28][CH:29]([CH3:31])[CH3:30])=O.[NH4+:32].[OH-:33]>C1COCC1>[C:29]([O:33][C:20]([NH:32][C:14](=[O:15])[C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH2:8])=[O:21])([CH3:31])([CH3:30])[CH3:28]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 89857Boc-L-methionine

Product 1

HCID 86586791HCID 86586791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution in THF (160 mL) of N-tert-butoxycarbonylmethionine (4.0.g, 16 mmol) was added N-methylmorpholine (1.84 mL, 16.2 mmol) and isobutyl chloroformate (2.1 mL, 16.2 mmol) and the reaction mixture was stirred for 20 minutes at 0° C. Concentrated NH4OH (7 mL) was added and stirring was continued at 0° C. for 2 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous 1M H3PO4. The organic phase was washed twice with saturated aqueous sodium bicarbonate (2×) and brine, dried, filtered and concentrated to give N-tert-butoxycarbonylmethionine amide (3.43 g) as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued at 0° C. for 2 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and aqueous 1M H3PO4
  5. washThe organic phase was washed twice with saturated aqueous sodium bicarbonate (2×) and brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b6da63ac6e4a4c8bbf05af7f397161b2
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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