Trifluoroacetic acid → HCID 11856681, compound

HRID 736831Notes

Reaction equation

HRID 736831 reaction equation
FC(F)(F)C(O)=O.C([O:12][NH:13][C:14]([C@:16]1([OH:45])[C@H:21]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=[C:36]([CH3:44])[CH:35]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:20][CH2:19][NH:18][CH2:17]1)=[O:15])(C)(C)C.FC(F)(F)C(O)=O>>[OH:12][NH:13][C:14]([C@:16]1([OH:45])[C@H:21]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=[C:36]([CH3:44])[CH:35]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:20][CH2:19][NH:18][CH2:17]1)=[O:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86607896HCID 86607896, compound

Product 1

HCID 11856681HCID 11856681, compoundYield 22%

Procedure

(3R,4R)-N-tert-Butoxy-3-hydroxy-4-(4-((2-methylquinolin-4-yl) methoxy)phenylsulfonamido)piperidine-3-carboxamide trifluoroacetic acid salt (Example 46, Step 8) was treated with neat trifluoroacetic acid (3 mL) at 45° C. for 5 days. After removal of trifluoroacetic acid, the residue was purified using preparative HPLC, eluting with a gradient of 10-30% acetonitrile with triethylamine (10 min) to yield 17.2 mg (22%) of (3R,4R)-N,3-dihydroxy-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-3-carboxamide as white powder. HRMS: calcd for C23H26N4O6S+H+, 487.16458; found (ESI-FTMS, [M+H]1+), 487.1646

Workup

  1. customAfter removal of trifluoroacetic acid
  2. customthe residue was purified
  3. washeluting with a gradient of 10-30% acetonitrile with triethylamine (10 min)

Sources & evidence

ORD record
ord-db7a0abe5cda4a968b6b6a4d2bbe9221
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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