4-Methylmorpholine → HCID 86742036, compound

HRID 568991Notes

Reaction equation

HRID 568991 reaction equation
[F:1][CH:2]([CH:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:18]=[CH2:19])[CH2:3][CH2:4][CH:5]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:6]([OH:8])=O.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[C:55]([O:59][C:60](=[O:64])[C@H:61]([CH3:63])[NH2:62])([CH3:58])([CH3:57])[CH3:56].CN1CCOCC1>ClCCl>[C:55]([O:59][C:60](=[O:64])[C@H:61]([CH3:63])[NH:62][C:6](=[O:8])[C@H:5]([CH2:4][CH2:3][CH:2]([F:1])[CH:17]([CH:18]=[CH2:19])[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:58])([CH3:57])[CH3:56]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11275390tert-Butyl alaninate hydrochlorideHCID 53927078HCID 53927078, compound

Product 1

HCID 86742036HCID 86742036, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound 5-fluoro-2,6-di-tert-butoxycarbonylamino-7-octenoic acid, 26, prepared as in Example II above (636 mg, 1.63 mmoles), 1-hydroxybenzotriazole monohydrate (250 mg) and dry dichloromethane (30 mL) are stirred at room temperature for 15 minutes. After cooling to 0° C., dicyclohexylcarbodiimide (370 mg) is added and stirring is continued for 1 hour at 0° C. and for 2 hours at room temperature. After cooling to 0° C. again, L-alanine-tert-butylester, hydrochloride (296 mg) is added, followed by N-methylmorpholine (330 mg). The mixture is stirred for 1 hour at 0° C., then at room temperature overnight. Filtration, washing (NaHCO3, NaHSO4, water), drying (Na2SO4) and evaporation yields an oil. This oil is dissolved in dichloromethane, filtered and evaporated. This last procedure is repeated several times to completely remove the DCU, leaving the title compound as an oil, 800 mg (95%).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringstirring
  3. waitis continued for 1 hour at 0° C. and for 2 hours at room temperature
  4. temperatureAfter cooling to 0° C. again
  5. stirringThe mixture is stirred for 1 hour at 0° C.
  6. customat room temperature
  7. customovernight
  8. filtrationFiltration
  9. washwashing (NaHCO3, NaHSO4, water)
  10. customdrying
  11. custom(Na2SO4) and evaporation
  12. customyields an oil
  13. filtrationfiltered
  14. customevaporated
  15. customto completely remove the DCU

Sources & evidence

ORD record
ord-dadb8da69c4742fd8894a99cc12170fd
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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