Water → HCID 118157132, compound

HRID 1779248Notes

Reaction equation

HRID 1779248 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:20][C:21]([C@@H:23](/[CH:37]=[CH:38]/[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]2([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])OCC[O:46]2)[C@@:24]([OH:36])([CH2:32][CH2:33][O:34][CH3:35])[C:25]([O:27]C(C)(C)C)=[O:26])=[O:22])[C:14]([NH:16][CH2:17][CH2:18][OH:19])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].O.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:20][C:21]([C@@H:23](/[CH:37]=[CH:38]/[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45](=[O:46])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C@@:24]([OH:36])([CH2:32][CH2:33][O:34][CH3:35])[C:25]([OH:27])=[O:26])=[O:22])[C:14](=[O:15])[NH:16][CH2:17][CH2:18][OH:19])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 118263504HCID 118263504, compound

Product 1

HCID 118157132HCID 118157132, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,3S,E)-tert-Butyl 3-((S)-3-(4-(but-2-ynyloxy)phenyl)-1-(2-hydroxyethylamino)-1-oxopropan-2-ylcarbamoyl)-11-(2-heptyl-1,3-dioxolan-2-yl)-2-hydroxy-2-(2-methoxyethyl)undec-4-enoate (11.3 mg, 0.014 mmol) was dissolved in dichloromethane (0.5 mL), and water (50 μL) was added. Trifluoroacetic acid (1.5 mL) was further added. The reaction mixture was stirred at room temperature for 5 hours, and then concentrated. The resulting residue was dissolved in methanol (1.0 mL). To the solution was added an aqueous solution (50 μL) of 28% ammonia and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated, and the resulting residue was then diluted in ethyl acetate, and washed with an aqueous solution of 0.5 M citric acid. The separated organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, then filtered, and concentrated. The resulting residue was purified by diol silica gel thin layer chromatography (dichloromethane/methanol) to obtain the target compound as colorless oil at a yield of 80%.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in methanol (1.0 mL)
  3. additionTo the solution was added an aqueous solution (50 μL) of 28% ammonia
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. concentrationThe reaction mixture was concentrated
  6. additionthe resulting residue was then diluted in ethyl acetate
  7. washwashed with an aqueous solution of 0.5 M citric acid
  8. washThe separated organic layer was washed with a saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe resulting residue was purified by diol silica gel thin layer chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-1c9b97039b1f458bb7ed0f0e6fc7bf4a
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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