Hydrochloric Acid → HCID 67440386, compound

HRID 1471565Notes

Reaction equation

HRID 1471565 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-046e0776b17140f1a9d1ffa640cbd382
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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