Sodium Bicarbonate → HCID 20786509, compound

HRID 2182868Notes

Reaction equation

HRID 2182868 reaction equation
[N+](C1C=C(S(CC[O:15][C:16](=[O:78])[CH:17]([NH:37][C:38](=[O:77])[CH2:39][O:40][C:41]2[CH:46]=[C:45]([CH3:47])[C:44]([S:48]([N:51]3[C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=4[N:53]=[C:52]3[S:60]([CH2:62][C:63]3[C:68]([CH3:69])=[C:67]([O:70][CH2:71][C:72]([F:75])([F:74])[F:73])[CH:66]=[CH:65][N:64]=3)=[O:61])(=[O:50])=[O:49])=[C:43]([CH3:76])[CH:42]=2)[CH2:18][CH2:19][C:20]([O:22]CCS(C2C=CC=C([N+]([O-])=O)C=2)(=O)=O)=[O:21])(=O)=O)C=CC=1)([O-])=O.C([O-])(O)=O.[Na+:83]>C1COCC1.O>[Na+:83].[CH3:47][C:45]1[CH:46]=[C:41]([CH:42]=[C:43]([CH3:76])[C:44]=1[S:48]([N:51]1[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2[N:53]=[C:52]1[S:60]([CH2:62][C:63]1[C:68]([CH3:69])=[C:67]([O:70][CH2:71][C:72]([F:73])([F:74])[F:75])[CH:66]=[CH:65][N:64]=1)=[O:61])(=[O:50])=[O:49])[O:40][CH2:39][C:38]([NH:37][CH:17]([CH2:18][CH2:19][C:20]([O-:22])=[O:21])[C:16]([O-:78])=[O:15])=[O:77].[Na+:83]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20786550HCID 20786550, compound2×

Product 1

HCID 20786509HCID 20786509, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 2-[2-(3,5-dimethyl-4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]-pentanedioic acid bis-[2-(3-nitro-benzenesulfonyl)-ethyl]ester (Intermediate 34, 800 mg, 0.69 mmol) and NaHCO3 (120 mg, 1.41 mmol, 2.05 eq) in THF-H2O (6 mL-3 mL) was heated to 70° C. for 3 h. Thereafter volatile materials were removed by evaporation under reduced pressure, the residual semi-solid was treated with EtOAc, and the mixture was filtered to remove undissolved materials. The filtrate was concentrated to total volume of about 3 mL, and then diethyl ether was added to the mixture. A solid precipitate formed and was collected by filtration to give Compound 13 (400 mg, 73%) as an off-white solid.

Workup

  1. customThereafter volatile materials were removed by evaporation under reduced pressure
  2. additionthe residual semi-solid was treated with EtOAc
  3. filtrationthe mixture was filtered
  4. customto remove undissolved materials
  5. concentrationThe filtrate was concentrated to total volume of about 3 mL
  6. additiondiethyl ether was added to the mixture
  7. customA solid precipitate formed
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ec01f3df5de14a6f8390f73b4107444e
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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