Trifluoroacetic acid → HCID 59164834, compound

HRID 1690096Notes

Reaction equation

HRID 1690096 reaction equation
CC(OC([NH:8][C@@H:9]([CH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[CH:20][CH:19]=1)=O)[C:10]([O:12][CH3:13])=[O:11])=O)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]2[CH2:15][CH2:14][C@@H:9]([C:10]([O:12][CH3:13])=[O:11])[N:8]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59164850HCID 59164850, compound

Product 1

HCID 59164834HCID 59164834, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-5-oxopentanoate (D31, 339 g) in dry DCM (3390 mL), at 0° C., was added trifluoroacetic acid (TFA) (640 mL) dropwise. The mixture was allowed to warm to room temperature and stirred for 2 hrs. Solvent and excess TFA were removed under vacuum and the resulting dark oil was stripped with EtOAc (1700 mL) and left overnight under high vacuum. The title compound was obtained as a red oil (818 g). 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.16 (m, 2H); 7.60 (td, 1H); 7.46 (m, 1H); 7.34 (m, 2H); 7.27 (m, 2H); 5.32 (s, 2H); 5.25 (m, 1H); 3.77 (s, 3H); 3.57 (m, 2H); 2.60 (m, 1H); 2.34 (m, 1H).

Workup

  1. customSolvent and excess TFA were removed under vacuum
  2. waitleft overnight under high vacuum

Sources & evidence

ORD record
ord-a4a7d53549ef410181e4567ad10de7fa
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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