Water → Benzyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylate

HRID 1964671Notes

Reaction equation

HRID 1964671 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14]2[NH:18][C:17]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[CH:16][CH:15]=2)[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1.[CH:29]([Si:32](Cl)([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])([CH3:31])[CH3:30].C(N(CC)CC)C.O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:12][O:11][CH2:10][C@H:9]([CH3:13])[O:8][C:6]1[CH:5]=[C:4]([C:14]2[NH:18][C:17]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[CH:16][CH:15]=2)[CH:3]=[C:2]([O:1][Si:32]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[CH:29]([CH3:31])[CH3:30])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 66682563Benzyl 5-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrole-2-carboxylate

Product 1

HCID 66680782Benzyl 5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxylateYield 89.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzyl 5-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrole-2-carboxylate (27.35 g, 71.7 mmol) synthesized in Example (106a) was dissolved in methylene chloride (350 mL), and triisopropylsilyl chloride (18.4 mL, 86.0 mmol), triethylamine (30.0 mL, 215 mmol) and 4-dimethylaminopyridine (10.53 g, 86.2 mmol) were added, followed by stirring at room temperature for 4 hours under nitrogen atmosphere. Water (400 mL) was added to separate the solution, and the organic layer was washed with saturated brine, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=3%-20%) to afford the desired product (34.41 g, yield 89%) as a pale yellow oil.

Workup

  1. customto separate the solution
  2. washthe organic layer was washed with saturated brine
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=3%-20%)

Sources & evidence

ORD record
ord-901e72dcfe4c463da2fc135ea2f87c0b
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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