Triethylamine → HCID 58065478, compound

HRID 909471Notes

Reaction equation

HRID 909471 reaction equation
[OH:1][CH:2]([CH2:7][NH:8][C:9]([C:11]1[NH:12][C:13]([C:16]2[CH:21]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[CH:19]=[C:18]([O:33][C@@H:34]([CH3:38])[CH2:35][O:36][CH3:37])[CH:17]=2)=[CH:14][CH:15]=1)=O)[C:3]([O:5][CH3:6])=[O:4].CS(OS(C)(=O)=O)(=O)=O.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:37][O:36][CH2:35][C@H:34]([CH3:38])[O:33][C:18]1[CH:17]=[C:16]([C:13]2[NH:12][C:11]([C:9]3[O:1][CH:2]([C:3]([O:5][CH3:6])=[O:4])[CH2:7][N:8]=3)=[CH:15][CH:14]=2)[CH:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 66890571HCID 66890571, compound

Product 1

HCID 58065478HCID 58065478, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-hydroxy-3-{[(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)carbonyl]amino}propanoate (686 mg, 1.26 mmol) synthesized in Example (27a) was dissolved in tetrahydrofuran (15 mL), and methanesulfonic anhydride (330 mg, 1.89 mmol) and triethylamine (0.53 mL, 3.80 mmol) were added, followed by stirring at room temperature for 19 hours under nitrogen atmosphere. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added, and the solution was separated with ethyl acetate (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=30%-70%) to afford the desired product (586 mg, yield 88%) as a white solid.

Workup

  1. customthe solution was separated with ethyl acetate (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=30%-70%)

Sources & evidence

ORD record
ord-3f4efdf6401a4dccb16d6008f46545b8
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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