4-Methoxybenzyl 2,2,2-Trichloroacetimidate → HCID 57887025, compound

HRID 1818868Notes

Reaction equation

HRID 1818868 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH:9]([OH:28])[CH:10]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:3][CH:2]=1.ClC(Cl)(Cl)C(=N)O[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1>O1CCCC1.B(F)(F)F.CCOCC>[C:1]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH:9]([O:28][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[CH:10]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:22])[CH3:23])[C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 110872634-Methoxybenzyl 2,2,2-TrichloroacetimidateHCID 57887021HCID 57887021, compound

Product 1

HCID 57887025HCID 57887025, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalyst3×HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride etherate (8.0 μL, 65 μmol) was added to a stirred solution of tert-butyl 5-biphenyl-4-yl-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-hydroxypentanoate (7.88 g, 16.3 mmol) and 4-methoxybenzyl 2,2,2-trichloroethanimidoate (6.88 g, 24.5 mmol) in tetrahydrofuran (40 mL) at 0° C. under nitrogen. The reaction was allowed to warm to room temperature at which stirring was continued for 2 h. A further portion of boron trifluoride etherate (8.0 μL, 65 μmol) was then added and stirring was continued at room temperature for a further 2 h. Two further additions of boron trifluoride etherate (8.0 μL, 65 μmol) followed by stirring at room temperature for 2 h were carried out before evaporation of the solvent. The residue was chromatographed on silica gel (5% to 10% diethyl ether: cyclohexane) to give the title compound (3.39 g, 34%) as a pale yellow oil which was a mixture of diastereomers. LC/MS: 4.81 min; z/e 605, calcd (M+1) 605. 1H NMR (400 MHz: CDCl3): 7.55 (2H), 7.45 (4H), 7.35-6.80 (7H), 4.50 (2H), 3.80 (3H), 3.60 (3H), 2.95 (1H), 2.80 (1H), 2.65 (1H), 1.85 (4H), 1.45 (9H), 0.85 (9H), 0.5 (6H).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for a further 2 h
  3. stirringby stirring at room temperature for 2 h
  4. customwere carried out before evaporation of the solvent
  5. customThe residue was chromatographed on silica gel (5% to 10% diethyl ether: cyclohexane)

Sources & evidence

ORD record
ord-77b6cfc9f09046e1996eb2a6ca675343
Source dataset
uspto-grants-2009_10
Patent number
US07601729B2

Reaction notes

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