Bicarbonate Ion → HCID 11682963, compound

HRID 1432333Notes

Reaction equation

HRID 1432333 reaction equation
O1[CH2:5][CH:4]=[CH:3][C:2]1=[O:6].[CH:7]([N-]C(C)C)([CH3:9])[CH3:8].[Li+].[C:15]([O:19][C:20](=[O:47])[NH:21][CH:22](S(C1C=CC=CC=1)(=O)=O)[CH2:23][C:24]1[CH:29]=[CH:28][C:27](OCC2C=CC=CC=2)=[CH:26][CH:25]=1)([CH3:18])([CH3:17])[CH3:16].[C:48](=[O:51])([OH:50])[O-].[CH2:52]1[CH2:56]OC[CH2:53]1>CCOC(C)=O>[C:15]([O:19][C:20](=[O:47])[NH:21][C@H:22]([C@@H:56]1[CH:52]=[CH:53][C:48](=[O:51])[O:50]1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([O:6][CH2:2][C:3]2[CH:4]=[CH:5][CH:9]=[CH:7][CH:8]=2)[CH:29]=1)([CH3:16])([CH3:17])[CH3:18]

Participants

7

Reactant 5

HCID 769Bicarbonate IonHCID 8028Tetrahydrofuran3×HCID 103412(5H)-FuranoneHCID 2724682Lithium diisopropylamideHCID 68886987HCID 68886987, compound

Product 1

HCID 11682963HCID 11682963, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5H-Furan-2-one (11.2 ml, 160 mmol, 2 eq) in THF (60 ml) is added slowly to a solution of lithium diisopropylamide (80 ml commercial 2M solution in THF/heptane/ethylbenzene, 160 mmol, 2 eq) in THF (180 ml) at −78° C. The mixture is stirred for another 20 min at −78° C. before [1-Benzenesulfonyl-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (37.3 g, 80 mmol) in THF (220 ml) is added at the same temperature. After stirring for another 45 min at −78° C. aqueous bicarbonate solution is added and the reaction mixture is taken up into EtOAc. The organic layer is washed with bicarbonate and brine and dried over magnesium sulfate. Evaporation of the solvent gives a residue that is purified by chromatography on silica using hexan/EtOAc 9/1 to 7/3. The product is recrystallized from ether/hexane to give the product as white crystals (11.1 g)

Workup

  1. additionis added at the same temperature
  2. additionis added
  3. washThe organic layer is washed with bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgives a residue that
  7. customis purified by chromatography on silica
  8. customThe product is recrystallized from ether/hexane

Sources & evidence

ORD record
ord-d5b7f174b16d4a4eb16da42231b60cfa
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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