Triethylamine → HCID 68806399, compound

HRID 2217436Notes

Reaction equation

HRID 2217436 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[C:21]([OH:23])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[C:27]([F:32])[CH:26]=1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[C:21](=[O:23])[NH:29][C:28]1[CH:30]=[CH:31][C:25]([Br:24])=[CH:26][C:27]=1[F:32])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 1230504-Bromo-2-fluoroanilineHCID 68806846HCID 68806846, compound

Product 1

HCID 68806399HCID 68806399, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (4.45 g, 12.9 mmol) was dissolved in 50 mL dry CHCl3 under an Ar atmosphere, added 4-bromo-2-fluoroaniline (2.45 g, 12.9 mmol), EEDQ (3.8 g, 15 mmol), and triethylamine (2.6 mL, 19.3 mmol). Reaction was refluxed for 6 hours, cooled and concentrated. Redissolved in EtOAc (250 mL), washed with 10% HCl (2×200 mL), 0.1M NaOH (2×200 mL), water, brine, dried with MgSO4, filtered and concentrated to yield title compound. (5.5 g, 82%) APCI (AP−): 515.1, 517.1 (M−H)−.

Workup

  1. customReaction
  2. temperaturewas refluxed for 6 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionRedissolved in EtOAc (250 mL)
  6. washwashed with 10% HCl (2×200 mL), 0.1M NaOH (2×200 mL), water, brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-76f497bc8bd944a3a7177c21d25c15ab
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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