HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → 6-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetylamino]hexanoic Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester | HCID 20786375 | — |
| Solvent | CH3CN-H2O iPrOH | HCID 22159075 | — |
| Product | 6-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetylamino]hexanoic Acid | HCID 22479303 | 43.1% |
Reaction Steps
A solution of 6-[2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 20, 450 mg, 0.50 mmol) and of NaHCO3 (50 mg, 0.60 mmol, 1.2 eq) in CH3CN-H2O-iPrOH (2 mL:1 mL:1 mL) was heated to 70° C. for 1.5 h. Thereafter volatile materials were removed by evaporation, the residual gummy oil was dissolved in CH2Cl2, and the mixture was filtered to remove undissolved solid. The filtrate was dried and concentrated under reduced pressure. The residual oil was purified by silica gel column to yield 150 mg of Compound 7 as a light brown foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06897227B2 |
| Source dataset | uspto-grants-2005_05 |
| ORD ID | ord-631870ad0585409d8c3f4e6ea9f94fdd |
| Source note | uspto-grants-2005_05 |