Trifluoroacetic acid → HCID 57161951, compound

HRID 1375015Notes

Reaction equation

HRID 1375015 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][C@H:18]([CH2:22][O:23][CH3:24])[CH2:17]2)[CH2:10][C@H:9]1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([O:33][Si:34]([C:47]([CH3:50])([CH3:49])[CH3:48])([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:27]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Si:34]([O:33][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[CH3:32])[CH2:25][C@@H:9]1[CH2:10][N:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][C@H:18]([CH2:22][O:23][CH3:24])[CH2:17]2)[CH2:12][CH2:13][NH:8]1)([C:47]([CH3:48])([CH3:49])[CH3:50])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57085168HCID 57085168, compound

Product 1

HCID 57161951HCID 57161951, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-1-tert-butoxycarbonyl-2-(3-tert-butyldiphenylsilyloxy-4-methylbenzyl)-4-[2-[(2S)-2-methoxymethylmorpholino]ethyl]piperazine (13.43 g) in dichloromethane (67.0 ml) was added trifluoroacetic acid (67.0 ml) at 0° C. After stirring at room temperature for 30 minutes, the mixture was concentrated and was added dropwise saturated aqueous sodium hydrogen carbonate solution. After stirring at room temperature for 30 minutes, the mixture was extracted with dichloromethane (100 ml×1, 50 ml×2). The combined extracts were dried over magnesium sulfate and evaporated under reduced pressure to give (2R)-2-(3-tert-butyldiphenylsilyloxy-4-methylbenzyl)-4-[2-[(2S)-2-methoxymethylmorpholino]ethyl]piperazine (11.63 g) as a brown oil.

Workup

  1. concentrationthe mixture was concentrated
  2. additionwas added dropwise saturated aqueous sodium hydrogen carbonate solution
  3. stirringAfter stirring at room temperature for 30 minutes
  4. extractionthe mixture was extracted with dichloromethane (100 ml×1, 50 ml×2)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d16f5620be464fd5aea5e71e73ab0300
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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