Sodium Bicarbonate → HCID 57475688, compound

HRID 217994Notes

Reaction equation

HRID 217994 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([F:43])=[C:21]([C@@:23]23[N:32]=[C:31]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[S:30][CH2:29][C@@H:28]2[CH2:27][C@H:26]([CH2:41]O)[O:25][CH2:24]3)[CH:22]=1)([O-:16])=[O:15].NC1C=CC(F)=C([C@@]23N=C(NC(=O)OC(C)(C)C)SC[C@@H]2[C@@H](OC)COC3)C=1.C(=O)(O)[O-].[Na+]>ClCCl>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([F:43])=[C:21]([C@@:23]23[N:32]=[C:31]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:39])[CH3:37])[S:30][CH2:29][C@@H:28]2[CH2:27][C@H:26]([CH2:41][F:11])[O:25][CH2:24]3)[CH:22]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 59281190HCID 59281190, compoundHCID 59281215HCID 59281215, compound

Product 1

HCID 57475688HCID 57475688, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[Bis(2-methoxyethyl)amino]sulfur trifluoride (285 μl) was added dropwise to a solution of tert-butyl [(4aR,6R,8aS)-8a-(5-nitro-2-fluorophenyl)-6-hydroxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate obtained in Preparation Example 13 (575 mg) in dichloromethane (55 ml) at −78° C. The mixture was stirred overnight with gradual heating to room temperature. A sodium bicarbonate solution was added to the reaction solution, and the aqueous layer was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-silica gel column chromatography to obtain the title compound (240 mg).

Workup

  1. extractionthe aqueous layer was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-00a68af702d8415a982ae1234d161e41
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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