Ethyl Acetate → HCID 67267564, compound

HRID 602790Notes

Reaction equation

HRID 602790 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Br:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)[CH3:5].[C:30]([O:34][C:35](=O)[O:36]C(C)(C)C)([CH3:33])([CH3:32])[CH3:31].CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1.CN(C1C=CN=CC=1)C>[C:30]([O:34][C:35]([N:9]1[C:8]2[CH2:7][CH:6]([C:4]([S:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)(=[O:22])=[O:21])([C:3]([O:2][CH3:1])=[O:29])[CH3:5])[CH2:18][CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([Br:19])[CH:14]=2)=[O:36])([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 67266713HCID 67266713, compound

Product 1

HCID 67267564HCID 67267564, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. customthe phases were separated
  2. extractionthe organic one was extracted with 1M KHSO4
  3. dry with materialThe organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6cd59af74ed645b8acb139ad49c60f63
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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