Triethylamine → HCID 89824779, compound

HRID 2277086Notes

Reaction equation

HRID 2277086 reaction equation
[C:1]([O:4][C@H:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6](Cl)=[O:7])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:20]([O:24][C:25](=[O:45])[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[CH2:35][NH:36][C:37]([C@@H:39]1[CH2:44][CH2:43][CH2:42][CH2:41][NH:40]1)=[O:38])([CH3:23])([CH3:22])[CH3:21]>C1COCC1>[C:1]([O:4][C@H:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([N:40]1[CH2:41][CH2:42][CH2:43][CH2:44][C@H:39]1[C:37](=[O:38])[NH:36][CH2:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[CH2:27][NH:26][C:25]([O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:45])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89824898HCID 89824898, compoundHCID 89835603HCID 89835603, compound

Product 1

HCID 89824779HCID 89824779, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−10° C.) solution of (2R)-1-chloro-3,3-dimethyl-1-oxobutan-2-yl acetate (0.15 g, 0.82 mmol) in THF (5 mL) was added triethylamine (0.54 mL, 3.90 mmol) and a solution of (S)-tert-Butyl-4-chloro-2-{(piperidine-2-carboxamido)methyl}benzylcarbamate (0.3 g, 0.78 mmol) in THF (2 mL) at −10° C. The reaction mixture was stirred at room temperature for 1 h then quenched with water (50 mL) and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by reverse phase combiflash column chromatography (C18, eluent: 0-10% acetonitrile water) to afford the title compound (0.27 g) as a white solid.

Workup

  1. customat −10° C
  2. customthen quenched with water (50 mL)
  3. extractionextracted with EtOAc (3×25 mL)
  4. washThe combined organic extracts were washed with brine solution (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse phase combiflash column chromatography (C18, eluent: 0-10% acetonitrile water)

Sources & evidence

ORD record
ord-d98c0eb35f454531b62703ba0f371951
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

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