Hydrochloric Acid → HCID 67440386, compound

HRID 1483716Notes

Reaction equation

HRID 1483716 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH3:36])[C:10]1[N:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]3[O:29][C:28](C)(C)C(C)(C)[O:26]3)=[C:21](C=O)[CH:20]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13])(C)(C)C.[BH4-].[Na+].Cl>CO>[OH:26][B:25]1[C:22]2[CH:23]=[CH:24][C:19]([O:18][C:16]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([N:9]([CH2:8][CH2:7][OH:6])[CH3:36])[N:17]=3)=[CH:20][C:21]=2[CH2:28][O:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636446HCID 86636446, compound

Product 1

HCID 67440386HCID 67440386, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of 11 (5.2 g, 9.7 mmol) in MeOH (anhydrous, 150 mL) was slowly added NaBH4 (2.2 g, 58 mmol). The reaction was stirred at room temperature for 4 hours, before the addition of HCl solution (1 M, 150 mL). The stirring was kept at room temperature overnight. Then the solution was slowly evaporated in vacuo. Purification was accomplished by reverse phase Biotage with 5%-100% MeOH/H2O gradient to afford 786 mg (25% yield) of the desired product as a white solid.

Workup

  1. customThen the solution was slowly evaporated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-021f19077620436396f9266c3f1b0f6d
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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