Trifluoroacetic acid → HCID 70097003, compound

HRID 1934405Notes

Reaction equation

HRID 1934405 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:47])[CH2:14][C@@H:15]([CH2:42][NH:43][C:44](=[O:46])[CH3:45])[NH:16][C:17]([C@@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:25](=[O:41])[CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)[CH2:20]1)=[O:18])(C)(C)C>>[NH:31]1[CH2:32][CH2:33][CH:28]([CH2:27][CH2:26][C:25]([N:21]2[CH2:22][CH2:23][CH2:24][C@@H:19]([C:17]([NH:16][C@H:15]([CH2:42][NH:43][C:44](=[O:46])[CH3:45])[CH2:14][C:13]([OH:47])=[O:12])=[O:18])[CH2:20]2)=[O:41])[CH2:29][CH2:30]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86758046HCID 86758046, compound

Product 1

HCID 70097003HCID 70097003, compoundYield 50%

Procedure

Trifluoroacetic acid (3 ml) was added to N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)propanoyl]-3-piperidylcarbonyl]-3(S)-acetylaminomethyl-β-alanine tert-butyl ester. The solvent was evaporated in vacuo. The residue was neutralized with saturated aqueous NaHCO3 and purified by HP-20 resin eluting with isopropanol/water (0-50% to give N-[(R)-1-[3-(4-piperidyl)propanoyl]-3-piperidylcarbonyl]-3(S)-acetylaminomethyl-β-alanine (120 mg, 50.0%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. custompurified by HP-20 resin
  3. washeluting with isopropanol/water (0-50%

Sources & evidence

ORD record
ord-3f26ff353dba4165baea2329e3043f9b
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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