Trifluoroacetic acid → HCID 57656789, compound

HRID 2371180Notes

Reaction equation

HRID 2371180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[O:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[O:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57656941HCID 57656941, compound

Product 1

HCID 57656789HCID 57656789, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (2S)-2-[(4-{[(3-chloro-4-fluorophenyl)amino]carbonyl}piperazin-1-yl)methyl]morpholine-4-carboxylate (9.867 g, 21.6 mmol) in dichloromethane (100 ml) was added TFA (100 ml). The reaction was allowed to stir at ambient temperature for 2 hours. The solvents were then removed in vacuo, residue partitioned between DCM and 2M NaOH, extracted twice and the combined organics dried (Na2SO4), filtered and evaporated to dryness to give the product as an off white solid (7.69 g, 21.6 mmol, 100%).

Workup

  1. customThe solvents were then removed in vacuo, residue
  2. custompartitioned between DCM and 2M NaOH
  3. extractionextracted twice
  4. dry with materialthe combined organics dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-5ae16f8800824c15808dd98a7c6b2db3
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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