Trifluoroacetic acid → N-hydroxy-2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxyphenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide trifluoroacetic acid salt

HRID 399345Notes

Reaction equation

HRID 399345 reaction equation
C([O:20][NH:21][C:22](=[O:63])[C@H:23]([N:44]([S:52]([C:55]1[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=1)(=[O:54])=[O:53])[CH2:45][C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1)[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]3[O:41][CH2:42][O:43][C:36]=23)=[O:31])[CH2:26][CH2:25]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.[F:71][C:72]([F:77])([F:76])[C:73]([OH:75])=[O:74]>C(Cl)Cl>[F:71][C:72]([F:77])([F:76])[C:73]([OH:75])=[O:74].[OH:20][NH:21][C:22](=[O:63])[C@H:23]([N:44]([S:52]([C:55]1[CH:56]=[CH:57][C:58]([O:61][CH3:62])=[CH:59][CH:60]=1)(=[O:54])=[O:53])[CH2:45][C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1)[CH:24]1[CH2:25][CH2:26][N:27]([C:30]([O:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]3[O:41][CH2:42][O:43][C:36]=23)=[O:31])[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86753206N-(trityl-oxy)-2-(R)-[(4-methoxybenzenesulfonyl) (4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxy-phenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide

Product 1

HCID 18665830N-hydroxy-2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxyphenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(trityloxy)-2-(R)-[(4-methoxybenzenesulfonyl) (4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxyphenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide (468 mg, 0.54 mmol) in methylene chloride (10 ml) cooled to 0° C. is added triethyl silane (0.17 ml, 1.08 mmol) followed by slow addition of trifluoroacetic acid (0.33 ml, 4.31 mmol). After stirring at 0° C. for 5 minutes, the solvent is removed in vacuo, at room temperature. The resulting white solid is dried on high vacuum for 1 hour and dissolved in the minimum amount of methylene chloride (ca. 2.5 ml). A mixture of diethyl ether (ca. 5 ml) and pentane (ca. 2.5 ml) is slowly added and the resulting white precipitate is triturated, filtered and washed with pentane (Note: this precipitation process must be repeated a second time if high purity is not obtained after the first attempt), to provide N-hydroxy-2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(2,3-methylenedioxyphenyl)-ethoxycarbonyl))-4-piperidinyl]acetamide trifluoroacetic acid salt.

Workup

  1. customthe solvent is removed in vacuo, at room temperature
  2. customThe resulting white solid is dried on high vacuum for 1 hour
  3. dissolutiondissolved in the minimum amount of methylene chloride (ca. 2.5 ml)
  4. additionA mixture of diethyl ether (ca. 5 ml) and pentane (ca. 2.5 ml)
  5. additionis slowly added
  6. customthe resulting white precipitate is triturated
  7. filtrationfiltered
  8. washwashed with pentane (
  9. customis not obtained after the first attempt),

Sources & evidence

ORD record
ord-451d550623df48728502a294b4acfaa9
Source dataset
uspto-grants-1998_10
Patent number
US05817822

Reaction notes

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