Trifluoroacetic acid → HCID 86650531, compound

HRID 1888142Notes

Reaction equation

HRID 1888142 reaction equation
COC1C=CC(C[N:8]([C@@H:12]([C@H:27]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:28]2[CH:29]=[N:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[CH2:13][CH2:14][C:15](=O)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)C(=O)[O-])=CC=1.FC(F)(F)C(O)=O>ClCCl>[Si:36]([O:35][C@@H:27]([C@H:12]1[CH2:13][CH2:14][C:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:8]1)[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[N:30][CH:29]=1)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86650532HCID 86650532, compound

Product 1

HCID 86650531HCID 86650531, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 18 g (28 mmol) of 4-methoxybenzyl[(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(6-chloropyridin-3-yl)methyl]-5-(4-nitrophenyl)-4-oxopentyl]carbamate from Step B in 75 mL of anhydrous dichloromethane was added 75 ml of trifluoroacetic acid. The resulting mixture was stirred at ambient temperature for 2 h during which time the reaction became dark red in color. All volatiles were removed in vacuo and the residue dissolved in 300 mL of dichloromethane. The solution was washed with a saturated aqueous sodium bicarbonate solution (2×100 mL), brine (100 ml) and then dried over magnesium sulfate and filtered. All volatiles were evaporated in vacuo to afford the title compound as a dark red gum (13 g, >99%) that was used immediately without further purification. LC-MS: m/z (ES) 460.4 (MH)+.

Workup

  1. customAll volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in 300 mL of dichloromethane
  3. washThe solution was washed with a saturated aqueous sodium bicarbonate solution (2×100 mL), brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customAll volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-ab65290855bf4060b47e37284103aa4a
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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