Toluene → HCID 57989118, compound

HRID 471287Notes

Reaction equation

HRID 471287 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([NH:20]C(=O)OC(C)(C)C)([CH3:19])[CH3:18])[CH:13]=[CH:14][CH:15]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[NH2:20][C:17]([CH3:19])([CH3:18])[CH2:16][C:12]1[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989221HCID 57989221, compound

Product 1

HCID 57989118HCID 57989118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl 1-(3-(hydroxymethyl)phenyl)-2-methylpropan-2-ylcarbamate (Example 275, step b) (0.7 g) in DCM (20 mL) and the resultant solution allowed to stand at 20° C. for 30 minutes. Toluene (40 mL) was added and the solvents evaporated under reduced pressure. The residue was partitioned between DCM and 1M aqueous sodium hydroxide, and the aqueous layer was extracted with DCM (×2). The combined organics were dried over sodium sulphate, filtered and the solvent removed under reduced pressure to afford the subtitled compound. Yield 0.440 g.

Workup

  1. customthe solvents evaporated under reduced pressure
  2. customThe residue was partitioned between DCM and 1M aqueous sodium hydroxide
  3. extractionthe aqueous layer was extracted with DCM (×2)
  4. dry with materialThe combined organics were dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-078dec110e5743d793e1e8d232acf7d2
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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