Water → HCID 118157648, compound

HRID 1779224Notes

Reaction equation

HRID 1779224 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](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]2([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])OCC[O:43]2)[C@:22]([CH2:31][CH2:32][F:33])([OH:30])[C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].O.S(=O)(=O)(O)O.C(OCC)(=O)C>C(#N)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:43])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C@:22]([CH2:31][CH2:32][F:33])([OH:30])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 90060353HCID 90060353, compound

Product 1

HCID 118157648HCID 118157648, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-(2-fluoro-ethyl)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate (21.0 mg, 0.0282 mmol) was dissolved in acetonitrile (1.0 mL), and water (0.01 mL, 0.556 mmol) and sulfuric acid (0.005 mL, 0.0938 mmol) were then added at room temperature. After stirring for 26 hours, ethyl acetate (10 mL) and water (10 mL) were added and the mixture was separated. The ethyl acetate layer was washed with a saturated aqueous solution (10 mL) of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was distilled off under reduced pressure. The obtained residue was purified by preparative TLC (diol, n-hexane/acetone=4/1) to obtain 2.3 mg of the title compound (0.00356 mmol, yield 13%) as a minor component.

Workup

  1. customthe mixture was separated
  2. washThe ethyl acetate layer was washed with a saturated aqueous solution (10 mL) of sodium chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by preparative TLC (diol, n-hexane/acetone=4/1)

Sources & evidence

ORD record
ord-f91ef02d0f3a431da483e10aa4ceac22
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…