Water → HCID 66682451, compound

HRID 1964556Notes

Reaction equation

HRID 1964556 reaction equation
[OH:1][C@H:2]([CH2:35][OH:36])[CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH:15]=[C:14]([O:29][C@@H:30]([CH3:34])[CH2:31][O:32][CH3:33])[CH:13]=2)=[CH:10][CH:11]=1)=[O:6].[CH:37]([Si:40](Cl)([CH:44]([CH3:46])[CH3:45])[CH:41]([CH3:43])[CH3:42])([CH3:39])[CH3:38].C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[OH:1][C@H:2]([CH2:35][O:36][Si:40]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:37]([CH3:39])[CH3:38])[CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=3)[CH:15]=[C:14]([O:29][C@@H:30]([CH3:34])[CH2:31][O:32][CH3:33])[CH:13]=2)=[CH:10][CH:11]=1)=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 66682235HCID 66682235, compound

Product 1

HCID 66682451HCID 66682451, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-[(2S)-2,3-Dihydroxypropyl]-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxamide (265 mg, 0.514 mmol) synthesized in Example (35a) was dissolved in dichloromethane (10 mL), and triisopropylsilyl chloride (0.12 mL, 0.691 mmol), triethylamine (0.21 mL, 1.51 mmol) and 4-dimethylaminopyridine (6.0 mg, 0.049 mmol) were added, followed by stirring at room temperature for 24 hours under nitrogen atmosphere. Water (10 mL) was added, and the solution was separated with dichloromethane (20 mL). The organic layer was washed with saturated brine, and subsequently dried 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=20%-50%) to afford the desired product (177 mg, yield 51%) as a white solid.

Workup

  1. customthe solution was separated with dichloromethane (20 mL)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried 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=20%-50%)

Sources & evidence

ORD record
ord-16a7b6ea9aa54d2497ea3c96e34ea074
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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