Sodium Bicarbonate → HCID 59281166, compound

HRID 217997Notes

Reaction equation

HRID 217997 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([F:41])=[C:19]([C@@:21]23[N:30]=[C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[S:28][CH2:27][C@@H:26]2[CH2:25][C@H:24]([CH2:39]O)[O:23][CH2:22]3)[CH:20]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([F:41])=[C:19]([C@@:21]23[N:30]=[C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:35])[CH3:36])[S:28][CH2:27][C@@H:26]2[CH2:25][C@H:24]([CH2:39][F:11])[O:23][CH2:22]3)[CH:20]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 59281207HCID 59281207, compound

Product 1

HCID 59281166HCID 59281166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[Bis(2-methoxyethyl)amino]sulfur trifluoride (155 μl) was added dropwise to a solution of tert-butyl [(4aR,6R,8aS)-8a-(5-bromo-2-fluorophenyl)-6-hydroxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate (200 mg) in dichloromethane (5.0 ml) at −78° C. The mixture was stirred overnight with gradual heating to room temperature. A sodium bicarbonate solution was added to the reaction mixture to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (145 mg).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a117831a453b4d688c071f9ba7d7764d
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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