Trifluoroacetic acid → HCID 69817782, compound

HRID 2417433Notes

Reaction equation

HRID 2417433 reaction equation
C(OC([N:8]([C@H:20]([CH2:43][O:44][Si](C)(C)C)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=2)[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:30])=[CH:24][CH:23]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCCl>[OH:44][CH2:43][C@@H:20]([NH:8][CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=2)[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:30])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69817624HCID 69817624, compound

Product 1

HCID 69817782HCID 69817782, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl 3-[[[[4-[(2S)-2-[N-(tert-butoxycarbonyl)-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-[(trimethylsilyl)oxy]propyl]phenyl]amino]carbonyl]amino]-benzoate (204 mg) in 1,2-dichloroethane (2.0 ml) was added trifluroacetic acid (2.0 ml) and the solution was stirred at room temperature for 1 hour. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate (10 ml). The solution was washed with aqueous saturated sodium bicarbonate solution (5 ml×1) and brine (10 ml×1) successively, dried over magnesium sulfate, and evaporated to give ethyl 3-[[[[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]propyl]phenyl]amino]carbonyl]amino]-benzoate (148 mg) as a white solid.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  3. washThe solution was washed with aqueous saturated sodium bicarbonate solution (5 ml×1) and brine (10 ml×1) successively
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-595f16faefb24f8aa256ba058f74dc8b
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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