HCID 118157159, compound → HCID 90060133, compound

HRID 1779156Notes

Reaction equation

HRID 1779156 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(O)=O)[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]>C(O)=O>[C:14]([O:16][CH2:17][CH2:43][C@:39]([OH:47])([C@@H:21]([C:19](=[O:20])[NH:18][C@H:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:11][CH:10]=1)/[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])[C:40]([OH:42])=[O:41])(=[O:15])[CH3:13]

Participants

3

Reactant 1

HCID 118157159HCID 118157159, compound

Product 1

HCID 90060133HCID 90060133, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

No. 5318799 (Compound R; 11.4 g, 15.4 mmol) was dissolved in formic acid (229 mL), and then the solution was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and then dissolved in ethyl acetate (250 mL). After washing twice with a 6:1 mixture (250 mL) of an aqueous solution of 1% sodium bicarbonate and a saturated aqueous solution of sodium chloride, the solution was washed with a 6:1 mixture (220 mL) of an aqueous solution of 10% ammonium chloride and a saturated aqueous solution of sodium chloride, and finally with a saturated aqueous solution of sodium chloride (100 mL), dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, dichloromethane/methanol) to obtain 10.5 g (15.3 mmol, 99% yield) of No. 5214354 (Compound S).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate (250 mL)
  3. washAfter washing twice with a 6:1 mixture (250 mL) of an aqueous solution of 1% sodium bicarbonate
  4. washa saturated aqueous solution of sodium chloride, the solution was washed with a 6:1 mixture (220 mL) of an aqueous solution of 10% ammonium chloride
  5. dry with materiala saturated aqueous solution of sodium chloride, and finally with a saturated aqueous solution of sodium chloride (100 mL), dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified on Biotage (silica gel, dichloromethane/methanol)
  9. customto obtain 10.5 g (15.3 mmol, 99% yield) of No

Sources & evidence

ORD record
ord-8460f93db8cb4d95a337a23c5c6ca860
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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