Water → HCID 11418746, compound

HRID 2095213Notes

Reaction equation

HRID 2095213 reaction equation
[CH:1]([C@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:18]=1)[CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[CH:1]([C@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:18]=1)[CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 12052Triethylsilane2×HCID 16660460HCID 16660460, compound

Product 1

HCID 11418746HCID 11418746, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (2S,7S)-trans-2-isopropyl-7-[4-methoxy-3-(3-methoxypropyloxy)-benzoyl]-8-methylnon-4-enoic acid (90 mg; 0.21 mmol) in trifluoroacetic acid (1 ml) was added triethylsilane (250 μl; 1.5 mmol). After stirring the solution at RT for 1 day, a second portion of triethylsilane (250 μl; 1.5 mmol) was added, and the solution was stirred at RT for a further 2 days and then added to water. The aqueous layer was extracted 3× with tert-butyl methyl ether and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica gel; hexane/acetone 4:1) to obtain (2S,7R)-trans-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnon-4-enoic acid (53 mg, 0.126 mmol, 61% yield).

Workup

  1. stirringthe solution was stirred at RT for a further 2 days
  2. extractionThe aqueous layer was extracted 3× with tert-butyl methyl ether
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (silica gel; hexane/acetone 4:1)

Sources & evidence

ORD record
ord-879d4b9caffd4757a3f409cc449dc783
Source dataset
uspto-grants-2013_05
Patent number
US08445708B2

Reaction notes

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