Hydrochloric Acid → HCID 11636062, compound

HRID 1096877Notes

Reaction equation

HRID 1096877 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[N:16](C(OC(C)(C)C)=O)[CH:10]([CH2:11][C:12]([C:39]3[S:43][C:42]([O:44][CH2:45][CH2:46][O:47][C:48]4[C:53]([Cl:54])=[CH:52][C:51]([CH3:55])=[CH:50][C:49]=4[Cl:56])=[N:41][CH:40]=3)=[C:13]2[C:24](=[O:38])[N:25]([CH:35]2[CH2:37][CH2:36]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])[CH2:9]1)=O)(C)(C)C.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH:35]1([N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])[C:24]([C:13]2[CH:14]3[NH:16][CH:10]([CH2:11][C:12]=2[C:39]2[S:43][C:42]([O:44][CH2:45][CH2:46][O:47][C:48]4[C:53]([Cl:54])=[CH:52][C:51]([CH3:55])=[CH:50][C:49]=4[Cl:56])=[N:41][CH:40]=2)[CH2:9][NH:8][CH2:15]3)=[O:38])[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68572080HCID 68572080, compound

Product 1

HCID 11636062HCID 11636062, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A sol. of compound F6 (3.29 mmol; 2.86 g) in CH2Cl2 (16.5 mL) at 0° C. was treated with HCl (4.0 M in dioxane; 16.5 mL, 66 mmol) and stirred for 1 h at rt. Sat. aq. Na2CO3 (100 mL) was added and the aq. layer was extracted with EtOAc (3×100 mL), dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC(CH2Cl2/MeOH 75:25) yielded the title compound (1.51 g, 68%). LC-MS: tR=0.89 min; ES+: 669.09.

Workup

  1. extractionthe aq. layer was extracted with EtOAc (3×100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC(CH2Cl2/MeOH 75:25)

Sources & evidence

ORD record
ord-de256465a7d64a93bd6c42d3d349c0d5
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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