Trifluoroacetic acid → HCID 69063812, compound

HRID 1436933Notes

Reaction equation

HRID 1436933 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([N:6]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])[C@@H:7]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)[CH2:2]1.FC(F)(F)C(O)=O.[C:37]([OH:46])(=[O:45])[C@@H:38]([C@H:40]([C:42]([OH:44])=[O:43])[OH:41])[OH:39]>ClCCl>[C:42]([C@@H:40]([C@H:38]([C:37]([OH:46])=[O:45])[OH:39])[OH:41])([OH:44])=[O:43].[O:1]1[CH2:5][CH2:4][C@@H:3]([N:6]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:27])([F:28])[F:29])[C@H:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 444305L-Tartaric acidHCID 86609374HCID 86609374, compound

Product 1

HCID 69063812HCID 69063812, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl (3R)-3-((3R)-tetrahydrofuran-3-yl{[2-(trifluoromethyl)phenyl]-methyl}amino)pyrrolidine-1-carboxylate (0.12 g, 0.29 mmol) in dichloromethane (4 mL) was added trifluoroacetic acid (2 mL). After stirring at room temperature for 3 h the solvent was removed in vacuo and the crude product taken up in methanol. This solution was absorbed onto a cationic ion exchange resin (Isolute™ SCX-2) and the basic components recovered from the column by elution with 2N ammonia in methanol. The eluate was evaporated, taken up again in methanol and L-tartaric acid (1 equivalent) added. The solvent was removed in vacuo and the resultant gum triturated with diethyl ether to yield the title compound as a pink microcrystalline solid. 1H NMR (300 MHz, CD3OD) δH: 7.82 (d, 1H), 7.57 (d, 1H), 7.53 (t, 1H), 7.32 (t, 1H), 4.31 (s, 2H), 3.92-3.82 (m, 3H), 3.70-3.47 (m, 5H), 3.37-3.22 (m, 2H), 3.17-3.03 (m, 1H), 2.94 (dd, 1H), 2.12-1.96 (m, 2H), 1.85-1.67 (m, 2H); MS: [M+H]=315.

Workup

  1. customwas removed in vacuo
  2. customThis solution was absorbed onto a cationic ion exchange resin (Isolute™ SCX-2)
  3. customthe basic components recovered from the column by elution with 2N ammonia in methanol
  4. customThe eluate was evaporated
  5. customThe solvent was removed in vacuo
  6. customthe resultant gum triturated with diethyl ether

Sources & evidence

ORD record
ord-09a3391a630d4c3db857cfa04a9dd4c2
Source dataset
uspto-grants-2009_11
Patent number
US07619096B2

Reaction notes

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