Sodium borohydride → HCID 67170637, compound

HRID 1918296Notes

Reaction equation

HRID 1918296 reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([NH:10][C:11]2([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])=[CH:6][C:5]=1[O:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([NH:10][C:11]2([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])=[CH:6][C:5]=1[O:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67170721HCID 67170721, compound

Product 1

HCID 67170637HCID 67170637, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of example 60 (300 mg, 0.686 mmol) was dissolved in methanol (6 ml) and cooled in an ice bath. Sodium borohydride (79 mg, 2.06 mmol) was added, the mixture was kept at 0° C. for 72 h, and then evaporated to dryness. The residue was partitioned between EA and 2 N hydrochloric acid, the aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was stirred with diethyl ether and the solidified material was filtered and dried in vacuo to yield the title compound (50 mg). From the mother liquor a further batch of the title compounds was isolated by RP HPLC (water/ACN gradient).

Workup

  1. temperaturecooled in an ice bath
  2. customevaporated to dryness
  3. customThe residue was partitioned between EA and 2 N hydrochloric acid
  4. extractionthe aqueous phase was extracted with EA
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. customevaporated to dryness
  7. filtrationthe solidified material was filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-2192c297f54a4d68a4017e01f6377c5e
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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