Trifluoroacetic acid → (2S)-2-Amino-5-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}hexanedioic acid

HRID 591307Notes

Reaction equation

HRID 591307 reaction equation
C(OC([NH:8][C@@H:9]([CH2:17][CH2:18][CH:19]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][F:37])=[CH:30][N:29]=1)[C:20]([O:22]C(C)(C)C)=[O:21])[C:10]([O:12]C(C)(C)C)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[NH2:8][C@@H:9]([CH2:17][CH2:18][CH:19]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][F:37])=[CH:30][N:29]=1)[C:20]([OH:22])=[O:21])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117812665Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}hexanedioate

Product 1

HCID 89155981(2S)-2-Amino-5-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}hexanedioic acidYield 44.5%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

To a solution of 56 mg of di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}hexanedioate (0.1 mmol) in anisol (0.7 mL) was added trifluoroacetic acid (1.5 mL), and the resulting mixture was stirred for 3 h at room temperature. Trifluoroacetic acid was removed under reduced pressure, water (approx. 2 mL) was added and separating anisol (which was expected to encumber preparative HPLC if present in large excess) was removed. The remaining aqueous solution of the crude product was directly loaded onto a preparative HPLC, method B, to give 14 mg of the target compound as white, hygroscopic lyophilisate (approx. 40% yield).

Workup

  1. customTrifluoroacetic acid was removed under reduced pressure, water (approx. 2 mL)
  2. additionwas added
  3. customseparating anisol (which was expected to encumber preparative HPLC if present in large excess)
  4. customwas removed

Sources & evidence

ORD record
ord-9685d1996dfa4661bdecdb318035f605
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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