Hydrochloric Acid → HCID 53918214, compound

HRID 1871850Notes

Reaction equation

HRID 1871850 reaction equation
[BH4-].[Li+].[O:3]=[C:4]([CH3:29])[CH2:5][N:6]1[C:15](=[O:16])[C:14]2[NH:13][C:12]([C:17]34[CH2:24][CH:23]5[CH2:25][CH:19]([CH2:20][CH:21]3[CH2:22]5)[CH2:18]4)=[N:11][C:10]=2[N:9]([CH2:26][CH2:27][CH3:28])[C:7]1=[O:8].Cl>>[OH:3][CH:4]([CH3:29])[CH2:5][N:6]1[C:15](=[O:16])[C:14]2[NH:13][C:12]([C:17]34[CH2:18][CH:19]5[CH2:25][CH:23]([CH2:22][CH:21]3[CH2:20]5)[CH2:24]4)=[N:11][C:10]=2[N:9]([CH2:26][CH2:27][CH3:28])[C:7]1=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 54266345HCID 54266345, compound

Product 1

HCID 53918214HCID 53918214, compoundYield 56%

Procedure

Lithium borohydride (102 mg, 4.22 mmol) was added under ice-cooling to 22 ml of a ethanolic solution of 780 mg (2.11 mmol) of Compound C obtained in Reference Example 1, followed by stirring at room temperature for 1.5 hours. The reaction solution was adjusted to pH 3 with 1N hydrochloric acid, and then extracted three times with chloroform. The extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized from acetonitrile to give 440 mg (yield 56%) of Compound D as white prisms.

Workup

  1. customobtained in Reference Example 1
  2. extractionextracted three times with chloroform
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained crude product
  7. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-a46eac25a3844ac7869a9777580338ba
Source dataset
uspto-grants-2000_08
Patent number
US06107064

Reaction notes

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