4-Methoxybenzyl 2,2,2-Trichloroacetimidate → HCID 57887023, compound

HRID 2382920Notes

Reaction equation

HRID 2382920 reaction equation
[CH3:1][C:2]([Si:5]([CH3:29])([CH3:28])[O:6][CH2:7][CH2:8][CH:9]([CH:17]([OH:27])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])[CH3:3].ClC(Cl)(Cl)C(=N)O[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1>O1CCCC1.B(F)(F)F.CCOCC>[CH3:4][C:2]([Si:5]([CH3:28])([CH3:29])[O:6][CH2:7][CH2:8][CH:9]([CH:17]([O:27][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1)[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 110872634-Methoxybenzyl 2,2,2-TrichloroacetimidateHCID 57887027HCID 57887027, compound

Product 1

HCID 57887023HCID 57887023, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalyst3×HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride etherate (5.0 μL, 39 μmol) was added to a stirred solution of 1,1-dimethylethyl 2-(2-{[(1,1-di methylethyl)(dimethyl)silyl]oxy}ethyl)-3-hydroxy-5-(4-iodophenyl)pentanoate (5.14 g, 9.63 mmol) and 4-methoxybenzyl 2,2,2-trichloroethanimidoate (4.05 g, 14.4 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 (5.0 μL, 39 μmol) was then added and stirring was continued at room temperature for a further 2 h. Two further additions of boron trifluoride etherate (5.0 μL, 39 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 (0% to 10% diethyl ether:cyclohexane) to give the title compound (4.14 g, 66%) as a yellow oil which was a mixture of diastereomers. LC/MS: 4.78 min; z/e 655, calcd (M+1) 655. 1H NMR (400 MHz: CDCl3): 7.55 (2H), 7.25 (2H), 6.90 (2H), 6.80 (2H), 4.55 (1H), 4.35 (1H), 3.80 (3H), 3.65 (1H), 3.55 (1H), 2.95 (1H major), 2.80 (1H minor), 2.70 (1H), 2.55 (1H), 1.95-1.60 (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 (0% to 10% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-a46e1984fca24ddb864168e9ee71728e
Source dataset
uspto-grants-2012_09
Patent number
US08263602B2

Reaction notes

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