Hydrochloric Acid → HCID 19972657, compound

HRID 2259901Notes

Reaction equation

HRID 2259901 reaction equation
[BH4-].[Na+].[ClH:3].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([C:21]2[C:30]3[O:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:27]([CH3:37])[C:26](=[O:38])[C:25]=3[CH:24]=[CH:23][CH:22]=2)=[O:20])[CH2:14][CH2:13]1.Cl.[OH-].[Na+]>CO>[ClH:3].[OH:20][CH:19]([C:21]1[C:30]2[O:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:27]([CH3:37])[C:26](=[O:38])[C:25]=2[CH:24]=[CH:23][CH:22]=1)[CH2:18][N:15]1[CH2:16][CH2:17][N:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH3:4])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 19972437HCID 19972437, compound

Product 1

HCID 19972657HCID 19972657, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.36 g of sodium borohydride was added portionwise at 0° to +5° C. to a solution of 15.5 g of the compound prepared in Example 1 in 1500 ml of methanol. After stirring for 90 minutes at 0° to +5° C., 3N aqueous hydrochloric acid solution was added in order slightly to acidify the reaction mixture, which was then stripped in vacuo. The residue was shaken with 2N aqueous sodium hydroxide solution and extracted with chloroform. The organic layer was dried on anhydrous sodium sulfate/calcium chloride, filtered, acidified with ethanolic hydrogen chloride and stripped in vacuo. After washing with diethyl ether, the crude product was crystallized from ethanol to give 9.5 g of title compound, m.p. 248°-249° C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried on anhydrous sodium sulfate/calcium chloride
  3. filtrationfiltered
  4. washAfter washing with diethyl ether
  5. customthe crude product was crystallized from ethanol

Sources & evidence

ORD record
ord-094d605cf04748a3b7bd60be4cae78d0
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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