Hydrochloric Acid → HCID 117874327, compound

HRID 2272877Notes

Reaction equation

HRID 2272877 reaction equation
[N:1]1([CH2:7][C@@H:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][N:9]2[C:18]([C:20]2[C:21]([C:29]3[N:37]4[C:32]([CH2:33][C:34](=[O:38])[CH2:35][CH2:36]4)=[C:31]([C:39]([O:41][CH3:42])=[O:40])[CH:30]=3)=[CH:22][C:23]3[O:27][CH2:26][O:25][C:24]=3[CH:28]=2)=[O:19])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[BH4-].[Na+].Cl>CO>[OH:38][CH:34]1[CH2:33][C:32]2[N:37]([C:29]([C:21]3[C:20]([C:18]([N:9]4[C@H:8]([CH2:7][N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[CH2:17][C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[CH2:10]4)=[O:19])=[CH:28][C:24]4[O:25][CH2:26][O:27][C:23]=4[CH:22]=3)=[CH:30][C:31]=2[C:39]([O:41][CH3:42])=[O:40])[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 117874166HCID 117874166, compound

Product 1

HCID 117874327HCID 117874327, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.55 g of the compound obtained in Step B (4.47 mmol) in 30 mL of methanol there are added in portions 558 mg (14.75 mmol) of sodium borohydride. The reaction mixture is stirred for one hour at ambient temperature. 50 mL of 1M HCl are subsequently added, and the methanol is evaporated off. The aqueous phase is subsequently neutralised with NaHCO3 and then extracted with dichloromethane. The organic phase is washed in succession with H2O, dried over MgSO4, filtered and concentrated to dryness. The oil so obtained is purified by flash chromatography (dichloromethane/ethanol-ammonia gradient). The title product is obtained in the form of a solid.

Workup

  1. customthe methanol is evaporated off
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed in succession with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe oil so obtained
  8. customis purified by flash chromatography (dichloromethane/ethanol-ammonia gradient)

Sources & evidence

ORD record
ord-ed1fe0fc3f514d39babad6d23bbde5d1
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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