Sodium borohydride → HCID 118260077, compound

HRID 1779214Notes

Reaction equation

HRID 1779214 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@H:21]([C@@:39]([OH:47])([CH2:43][C:44]([OH:46])=[O:45])[C:40]([OH:42])=[O:41])/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[BH4-].[Na+]>CO>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@H:21]([C@@:39]([OH:47])([CH2:43][C:44]([OH:46])=[O:45])[C:40]([OH:42])=[O:41])/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([OH:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118157159HCID 118157159, compound

Product 1

HCID 118260077HCID 118260077, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of No. 5153510, (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinic acid (20 mg, 0.0304 mmol) and methanol was added NaBH4 (7.4 mg, 0.196 mmol), and the mixture was stirred at room temperature. After confirming the consumption of the starting materials by LCMS, a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, and dried over anhydrous sodium sulfate. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by preparative HPLC, and then extracted with ethyl acetate. The organic layer was washed with a saturated brine, and then dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure to obtain the title compound (8 mg, 40%, colorless oil).

Workup

  1. additionTo a mixture of No
  2. customthe consumption of the starting materials by LCMS
  3. additiona saturated aqueous solution of ammonium chloride was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe filtrate was then concentrated under reduced pressure
  8. customThe resulting residue was purified by preparative HPLC
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with a saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationThe organic solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fc96115cc64c43949f54d14d9d9bf411
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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