Water → HCID 66681066, compound

HRID 1964665Notes

Reaction equation

HRID 1964665 reaction equation
[OH:1][C@H:2]([CH2:35][O:36][Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[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]=[N:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N: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.CS(O)(=O)=O.C(N(CC)CC)C.O>O1CCCC1>[CH3:33][O:32][CH2:31][C@H:30]([CH3:34])[O:29][C:14]1[CH:15]=[C:16]([CH:17]=[C:12]([C:9]2[NH:8][C:7]([C:5]3[O:1][C@@H:2]([CH2:35][O:36][Si:37]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:39])[CH3:40])[CH:44]([CH3:46])[CH3:45])[CH2:3][N:4]=3)=[CH:11][CH:10]=2)[CH:13]=1)[O:18][C:19]1[CH:24]=[N:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 66681177HCID 66681177, compound

Product 1

HCID 66681066HCID 66681066, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

N-{(2S)-2-hydroxy-3-[(triisopropylsilyl)oxy]propyl}-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrole-2-carboxamide (558 mg, 0.82 mmol) synthesized in Example (101b) was dissolved in tetrahydrofuran (20 mL), and anhydrous methanesulfonic acid (287 mg, 1.65 mmol) and triethylamine (0.34 mL, 2.47 mmol) were added, followed by stirring at 50° C. for 6 hours under nitrogen atmosphere. To the reaction solution, water (40 mL) was added, and extraction was carried out twice with methylene chloride (40 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: methanol/methylene chloride=0%-5%) to afford the desired compound (496 mg, yield 94%) as a white solid.

Workup

  1. extractionextraction
  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: methanol/methylene chloride=0%-5%)

Sources & evidence

ORD record
ord-c63d0d5139564b5d997ad7c5023b5400
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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