Potassium Carbonate → HCID 66934388, compound

HRID 1365489Notes

Reaction equation

HRID 1365489 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([F:27])[CH:18]=2)([NH2:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:34](Cl)(=[O:45])[O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]([NH:16][C:34](=[O:45])[O:35][C:36]2[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=2)([C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:20]=[C:19]([F:27])[CH:18]=2)[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 821294-Nitrophenyl chloroformateHCID 59134582(S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine

Product 1

HCID 66934388HCID 66934388, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine (0.15 g, 0.38 mmol) was dissolved in dichloromethane (5 mL) at room temperature. Solid powdered K2CO3 (0.52 g, 3.8 mmol) was added followed by 4-nitrophenyl carbonochloridate (0.11 g, 0.56 mmol). The resulting slurry was stirred at room temperature for 14 h, diluted with DCM (ca. 50 mL) and washed with sat. NaHCO3 (ca. 4×20 mL). The organic portion was dried over anhydrous Na2SO4, decanted and concentrated yielding (S)-4-nitrophenyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamate as a pale brown oil, (0.20 g, crude quantitative yield). LCMS: 2.26 min [M+1] 560.2 (2 min gradient, MeOH/H2O 0.1% TFA)

Workup

  1. washwashed with sat. NaHCO3 (ca. 4×20 mL)
  2. dry with materialThe organic portion was dried over anhydrous Na2SO4
  3. customdecanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a02db229766e494c9a7056b4ffbc2eee
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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