Formic Acid → HCID 118157648, compound

HRID 1779223Notes

Reaction equation

HRID 1779223 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].S(=O)(=O)(O)O.C(O)=O>C(#N)C.O.C(OCC)(=O)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

7

Reactant 3

HCID 284Formic AcidHCID 1118Sulfuric AcidHCID 90060353HCID 90060353, compound

Product 1

HCID 118157648HCID 118157648, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

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 (64.0 mg, 0.0855 mmol) was dissolved in acetonitrile (0.96 mL), and water (0.03 mL, 1.67 mmol) and sulfuric acid (0.016 mL, 0.300 mmol) were then added at room temperature. After stirring for 18.5 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. Formic acid (0.016 mL, 0.424 mmol) was added to the obtained residue (41.0 mg) at room temperature, and the mixture was then stirred for 21 hours. Formic acid was distilled off under reduced pressure. The residue was then purified by preparative HPLC and preparative TLC (diol, n-hexane/acetone=2/1) to obtain 15.9 mg of the title compound (0.0246 mmol, yield 29%).

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. stirringthe mixture was then stirred for 21 hours
  7. distillationFormic acid was distilled off under reduced pressure
  8. customThe residue was then purified by preparative HPLC and preparative TLC (diol, n-hexane/acetone=2/1)

Sources & evidence

ORD record
ord-a251f9a0ed97431d87110a78ac914475
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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