Trifluoroacetic acid → HCID 117684692, compound

HRID 1774616Notes

Reaction equation

HRID 1774616 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C@@H:16]([CH2:21][C:22]#[C:23][C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH:37]3[CH2:39][CH2:38]3)=[C:32]([Cl:40])[CH:31]=2)[N:27]=[CH:26][N:25]=1)[C:17]([O:19][CH3:20])=[O:18])=O)(C)(C)C>ClCCl>[NH2:15][C@@H:16]([CH2:21][C:22]#[C:23][C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH:37]3[CH2:39][CH2:38]3)=[C:32]([Cl:40])[CH:31]=2)[N:27]=[CH:26][N:25]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117684691HCID 117684691, compound

Product 1

HCID 117684692HCID 117684692, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6 ml) was added dropwise to a stirred solution of methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-5-[6-(3-chloro-4-cyclopropoxyphenyl)pyrimidin-4-yl]pent-4-ynoate (2.26 g, 4.8 mmol) in dichloromethane (20 ml) and the mixture was stirred at room temperature overnight. After this time the reaction mixture was concentrated and the resulting residue redissolved in DCM (20 ml) before being washed with saturated sodium bicarbonate. The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (1.64 g, 92% yield) as a brown oil. Tr=1.63 min m/z (ES+) (M+H+) 372, 373.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated
  2. dissolutionthe resulting residue redissolved in DCM (20 ml)
  3. washbefore being washed with saturated sodium bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-db2ed04f5a124a54a4f0d66066b98dcb
Source dataset
uspto-grants-2016_02
Patent number
US09260422B2

Reaction notes

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