Acetonitrile → HCID 118157288, compound

HRID 1779215Notes

Reaction equation

HRID 1779215 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:49])([CH2:43][CH2:44][C:45]([O:47]C)=[O:46])[C:40]([O-: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]C)=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C(#N)C.C(N(CC)CC)C.[Br-].[Li+]>O>[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:49])([CH2:43][CH2:44][C:45]([OH:47])=[O:46])[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]([OH:16])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 82050Lithium BromideHCID 131734864HCID 131734864, compound

Product 1

HCID 118157288HCID 118157288, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of No. 5507802, 5-methyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-pentanedioate (18 mg, 0.0262 mmol), acetonitrile (450 μL), and water (9 μL) were added triethylamine (21.9 μL, 0.157 mmol) and lithium bromide (45.6 mg, 0.525 mmol), and the mixture was stirred at 50° C. After confirming the consumption of No. 5507802 by LCMS, 0.1 M hydrochloric acid 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 SP1 (Diol cartridge, 80% ethyl acetate/n-hexane Rf=0.6) to obtain the title compound (9.6 mg, 56% yield, white solid).

Workup

  1. additionTo a mixture of No
  2. customthe consumption of No
  3. addition5507802 by LCMS, 0.1 M hydrochloric acid 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 SP1 (Diol cartridge, 80% ethyl acetate/n-hexane Rf=0.6)

Sources & evidence

ORD record
ord-47e1308662fb412a8891264735783b7d
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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