4-Methylmorpholine → HCID 53889410, compound

HRID 479484Notes

Reaction equation

HRID 479484 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.C[N:31]1CCOCC1.[OH-].[NH4+]>C1COCC1.[Cl-].[Na+].O>[NH2:31][C:13](=[O:14])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 102670N-[(Benzyloxy)carbonyl]-O-tert-butylserine

Product 1

HCID 53889410HCID 53889410, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-15 °C

Procedure

A stirred solution of racemic (2S)-2-(((benzyloxy)carbonyl)amino)-3-tert-butoxypropanoic acid (1.01 g, 3.43 mmol) in THF (10 mL) at −15° C. was treated with isobutyl chloroformate (0.440 mL, 3.43 mmol) followed by N-methylmorpholine (0.380 mL, 3.43 mmol). After 15 minutes, the milky white reaction mixture was treated dropwise with ammonium hydroxide (2.8 mL of 30% reagent, 5.0 mmol). The reaction flask was warmed to −15° C. and stirred for 45 minutes. The clear homogeneous mixture was treated with brine (20 mL) and extracted with ethyl acetate (2×40 mL). The organic portions were combined and washed with saturated aqueous NaHCO3 solution (15 mL) and brine (15 mL), and dried (MgSO4). Filtration and removal of solvent provided 928 mg of the desired product a white solid.

Workup

  1. extractionextracted with ethyl acetate (2×40 mL)
  2. washwashed with saturated 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-26e41cea6b44406295c16543c1ed32e5
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

Loading…