Trifluoroacetic acid → HCID 67080070, compound

HRID 655537Notes

Reaction equation

HRID 655537 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]([C:17](=[O:39])[N:18]([C@H:25]([CH2:36][O:37][CH3:38])[CH2:26][CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:19][CH:20](OC)OC)[CH3:16])(C)(C)C.C([SiH](CC)CC)C.C(N(CC)CC)C>ClCCl>[CH2:29]([O:28][CH2:27][CH2:26][C@H:25]([N:18]1[CH2:19][CH2:20][NH:14][C@@H:15]([CH3:16])[C:17]1=[O:39])[CH2:36][O:37][CH3:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 12052TriethylsilaneHCID 67079724HCID 67079724, compound

Product 1

HCID 67080070HCID 67080070, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (8.03 g, 70.4 mmol) was added at 0° C. to a solution of {(S)-1-[((S)-3-benzyloxy-1-methoxymethyl-propyl)-(2,2-dimethoxy-ethyl)-carbamoyl]-ethyl}-carbamic acid tert-butyl ester (2.20 g, 4.69 mmol) in dichloromethane (40 mL). The reaction mixture was allowed to reach room temperature over 2 h, then triethylsilane (2.73 g, 70.4 mmol) was added. The reaction mixture was stirred for 16 h at room temperature, then cooled to 0° C. and treated with triethylamine (7.24 g, 70.4 mmol). After 10 min the ice bath was removed and the reaction mixture evaporated. The residue was taken up in ethyl acetate/water and neutralized with 2 M aq. sodium carbonate solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chomatography (SiO2; dichloromethane-methanol gradient) afforded the title compound (735 mg, 51%). Light yellow oil, MS (ISP)=307.3 (M+H)+.

Workup

  1. temperaturecooled to 0° C.
  2. customAfter 10 min the ice bath was removed
  3. customthe reaction mixture evaporated
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5cb1fc3ccb6c4ff0959a96dd3b07da5a
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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