Sodium borohydride → HCID 131734863, compound

HRID 1779212Notes

Reaction equation

HRID 1779212 reaction equation
[Na].[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([NH:19][C:20]([C@@H:22](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:23]([OH:30])([CH2:27][CH2:28][OH:29])[C:24]([O-:26])=[O:25])=[O:21])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5].[K+:48].[BH4-].[Na+]>CO>[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([NH:19][C:20]([C@@H:22](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([OH:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:23]([OH:30])([CH2:27][CH2:28][OH:29])[C:24]([O-:26])=[O:25])=[O:21])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5].[K+:48]

Participants

5

Reactant 3

HCID 4311764Sodium borohydride2×HCID 5360545SodiumHCID 118157775HCID 118157775, compound

Product 1

HCID 131734863HCID 131734863, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of No. 5214357, a mixture of sodium and potassium (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (100 mg, 0.147 mmol) and methanol (5 mL) was added NaBH4 (5.5 mg, 0.146 mmol) at room temperature. After stirring for 1.5 hours, NaBH4 (5.5 mg, 0.146 mmol) was added again. After stirring for 30 minutes, the consumption of the starting materials was confirmed by LCMS. Water 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 to obtain the title compound (100 mg, yield 99% or more, white solid).

Workup

  1. additionTo a mixture of No
  2. stirringAfter stirring for 30 minutes
  3. customthe consumption of the starting materials
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-d5762390329349f4b0e39ef8d6196b6d
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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