Triethylamine → HCID 89824921, compound

HRID 2277097Notes

Reaction equation

HRID 2277097 reaction equation
[C:1]([O:4][C@H:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[C:19]([O:23][C:24](=[O:44])[NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[CH2:34][NH:35][C:36]([C@@H:38]1[CH2:43][O:42][CH2:41][CH2:40][NH:39]1)=[O:37])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:4][C@H:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([N:39]1[CH2:40][CH2:41][O:42][CH2:43][C@H:38]1[C:36](=[O:37])[NH:35][CH2:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[CH2:26][NH:25][C:24]([O:23][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:44])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 89824784HCID 89824784, compoundHCID 89835592HCID 89835592, compound

Product 1

HCID 89824921HCID 89824921, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (R)-2-acetoxy-3,3-dimethylbutanoic acid (0.14 g, 1.04 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (1.10 mL, 1.30 mmol) at 0° C. under nitrogen atmosphere and the resulting mixture was stirred at room temperature for 40 min. The reaction mixture was concentrated to dryness and the residue was dissolved in CH2Cl2 (4 mL). A solution of (S)-tert-Butyl-4-chloro-2-{(morpholine-3-carboxamido)methyl}benzylcarbamate (0.20 g, 0.52 mmol) and triethylamine (0.70 mL, 2.08 mmol) in CH2Cl2 (2 mL) was added dropwise at 0° C. and the reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed sequentially with saturated NaHCO3 solution (10 mL) and 1M aqueous HCl (10 mL). The organic layer was washed with brine solution (10 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 50% EtOAc/hexanes) to afford the title compound as a pale yellow oil (0.2 g).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in CH2Cl2 (4 mL)
  3. stirringto stir at room temperature for 16 h
  4. washwashed sequentially with saturated NaHCO3 solution (10 mL) and 1M aqueous HCl (10 mL)
  5. washThe organic layer was washed with brine solution (10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-32457dafa19d4308bdc04f051627f248
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

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