4-Methylmorpholine → HCID 18770761, compound

HRID 479478Notes

Reaction equation

HRID 479478 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH:3]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[C:4](O)=[O:5].ClC(OCC(C)C)=O.C[N:28]1CCOCC1.[OH-].[NH4+]>C1COCC1.[Cl-].[Na+].O>[NH2:28][C:4]([CH:3]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[C:2]([CH3:18])([CH3:17])[CH3:1])=[O:5]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 18770669HCID 18770669, compound

Product 1

HCID 18770761HCID 18770761, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-15 °C

Procedure

A stirred solution of Example 26A (458 mg, 1.84 mmol) in THF (10 mL) at −15° C. was treated with isobutyl chloroformate (0.240 mL, 1.84 mmol) followed by N-methylmorpholine (0.200 mL, 1.84 mmol). After 15 minutes, the milky white reaction mixture was treated dropwise with ammonium hydroxide (4.2 mL of 30% reagent, 15.0 mmol). The reaction flask was warmed to −15° C., stirred for 45 minutes, treated with brine (20 mL), and the clear homogeneous mixture was extracted with ethyl acetate (2×40 mL). The organic portions were combined, washed with aqueous KHSO4 solution (15 mL), aqueous NaHCO3 solution (15 mL), and brine (15 mL), and dried (MgSO4). Filtration and removal of solvent provided 232 mg of the desired product a white solid.

Workup

  1. extractionthe clear homogeneous mixture was extracted with ethyl acetate (2×40 mL)
  2. washwashed with aqueous KHSO4 solution (15 mL), aqueous NaHCO3 solution (15 mL), and brine (15 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and removal of solvent

Sources & evidence

ORD record
ord-3e57098954be42659ec8011e1b45f310
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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