HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 67267564, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Carbonic acid, bis(1,1-dimethylethyl) ester | HCID 10219638 | — |
| Reactant | HCID 67266713 | HCID 67266713 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67267564 | HCID 67267564 | 90% |
Reaction Steps
To 1.2 g (2.52 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester (from example 99) in 40 mL of THF were added 31 mg (0.25 mmol, 0.1 eq) of DMAP and 660 mg (3.02 mmol, 1.2 eq) of carbonic acid di-tert-butyl ester at 0° C. The reaction mixture was stirred at RT for 2 hours. EtOAc and a solution of aqueous NaHCO3 were added, the phases were separated, and the organic one was extracted with 1M KHSO4. The organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography afforded 1.3 g (90%) of (RS,SR)-2-(-1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-6-bromo-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester as white solid, MS: 575 (M,1Br).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07906546B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-6cd59af74ed645b8acb139ad49c60f63 |
| Source note | uspto-grants-2011_03 |