Trifluoroacetic acid → HCID 86638056, compound

HRID 1668602Notes

Reaction equation

HRID 1668602 reaction equation
O[CH:2]1[C:10]2[CH:9]=[C:8]3[CH2:11][CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][CH2:15][C:7]3=[CH:6][C:5]=2[C:4](=O)[N:3]1[CH:24]([CH3:26])[CH3:25].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:26][CH:24]([N:3]1[CH2:4][C:5]2[CH:6]=[C:7]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:8]3=[CH:9][C:10]=2[CH2:2]1)[CH3:25]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 59150482HCID 59150482, compound

Product 1

HCID 86638056HCID 86638056, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 1-hydroxy-2-(1-methylethyl)-3-oxo-2,3,5,6,8,9-hexahydroazepino[4,5-f]isoindole-7(1H)-carboxylate (1.0 g) and triethylsilane (0.95 ml) in DCM (20 ml), at 0° C., TFA (10 ml) was added dropwise and the mixture stirred for 1 h. the mixture was neutralized with 2M aqueous Na2CO3 and washed with ether discarding the organic layer. Then the aqueous layer was made basic with NaOH and extracted with DCM. The organic solution was washed with brine, dried over Na2SO4 and concentrated to afford a pale yellow solid (0.6 g, 88% yield).

Workup

  1. washwashed with ether discarding the organic layer
  2. extractionextracted with DCM
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea0b01bb21f34b18976a40b6f2f107b6
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

Loading…