Sodium Bicarbonate → HCID 86709398, compound

HRID 2172259Notes

Reaction equation

HRID 2172259 reaction equation
C(O)C.Cl.[N+:5]([C:8]1[N:9]=[C:10]2[N:15]([CH:16]=1)[CH2:14][CH2:13][C@H:12]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][CH:28]([CH2:31][CH:32]([O:44]C4CCCCO4)[C:33]4[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=4)[CH2:27][CH2:26]3)=[CH:21][CH:20]=1)[O:11]2)([O-:7])=[O:6].C(=O)([O-])O.[Na+]>>[N+:5]([C:8]1[N:9]=[C:10]2[N:15]([CH:16]=1)[CH2:14][CH2:13][C@H:12]([CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]3[CH2:30][CH2:29][CH:28]([CH2:31][CH:32]([C:33]4[CH:34]=[CH:35][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:37][CH:38]=4)[OH:44])[CH2:27][CH2:26]3)=[CH:23][CH:24]=1)[O:11]2)([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21887872Ethanol hydrochlorideHCID 86709399HCID 86709399, compound

Product 1

HCID 86709398HCID 86709398, compoundYield 92%

Procedure

A 1 N HCl ethanol solution (6 ml) was added to (R)-2-nitro-7-(4-{4-[2-(tetrahydropyran-2-yloxy)-2-(4-trifluoromethoxyphenyl)ethyl]piperidin-1-yl}phenoxymethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (0.20 g), and the mixture was stirred at room temperature for 3 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the residue obtained by distilling the solvent off, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The crystal thus obtained was washed with methylene chloride-ether and dried to afford the title compound as a white powder (0.16 g).

Workup

  1. customobtained
  2. distillationby distilling the solvent off,
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtering
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe crystal thus obtained
  9. washwas washed with methylene chloride-ether
  10. customdried

Sources & evidence

ORD record
ord-3fb2d404569d4cb68bee334358c3b952
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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