Acetic Anhydride → HCID 90060220, compound

HRID 1779221Notes

Reaction equation

HRID 1779221 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:19][C:20]([C@@H:22](/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C@@:23]([OH:34])([CH2:31][CH2:32][OH:33])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[C:52](OC(=O)C)(=[O:54])[CH3:53].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[C:52]([O:33][CH2:32][CH2:31][C@:23]([OH:34])([C@@H:22]([C:20](=[O:21])[NH:19][C@H:13]([C:14]([O:16][CH2:17][CH3:18])=[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:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])(=[O:54])[CH3:53]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 90060310HCID 90060310, compound

Product 1

HCID 90060220HCID 90060220, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (3.22 g, 4.51 mmol) was dissolved in dichloromethane (64 mL), and the mixture was then cooled to 0° C. in an ice bath. Acetic anhydride (1.07 mL, 11.3 mmol), triethylamine (0.63 mL, 4.52 mmol), and dimethylaminopyridine (55.1 mg, 0.451 mmol) were added in this order, and the mixture was then stirred at 0° C. for 1.5 hours. The mixture was quenched with water (46 mL), and then extracted with dichloromethane (46 mL). The organic layer was washed with a saturated aqueous solution (33 mL) of sodium chloride, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 2.65 g (3.51 mmol, 78% yield) of No. 5328456.

Workup

  1. customThe mixture was quenched with water (46 mL)
  2. extractionextracted with dichloromethane (46 mL)
  3. washThe organic layer was washed with a saturated aqueous solution (33 mL) of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)
  8. customto obtain 2.65 g (3.51 mmol, 78% yield) of No

Sources & evidence

ORD record
ord-5ebea87c19c34f25bb7e7c30f2d93767
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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