Acetic Anhydride → HCID 68520179, compound

HRID 20617Notes

Reaction equation

HRID 20617 reaction equation
[F:1][C@:2]12[C@@H:22]([O:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH2:21][C@@:20]3([CH3:30])[C@@H:12]([CH2:13][C@H:14]([CH3:32])[C@:15]3([OH:31])[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:34])[CH:4]=[CH:5][C:6](=[O:33])[CH:7]=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C1COCC1.CN(C1C=CN=CC=1)C>[F:1][C@:2]12[C@@H:22]([O:23][C:24](=[O:29])[C:25]([F:27])([F:26])[F:28])[CH2:21][C@@:20]3([CH3:30])[C@@H:12]([CH2:13][C@H:14]([CH3:32])[C@:15]3([OH:31])[C:16](=[O:19])[CH2:17][O:18][C:35](=[O:37])[CH3:36])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:34])[CH:4]=[CH:5][C:6](=[O:33])[CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 68517908HCID 68517908, compound

Product 1

HCID 68520179HCID 68520179, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 1-3 (122.5 g) in THF (1 L) at RT was added DMAP (6.0 g, 49 mmol) and acetic anhydride (50.2 g, 491 mmol) and the mixture allowed to stir for 15 hours. The solvent was evaporated, and the residue diluted with 1 L of water. The precipitate was isolated by filtration and dried for 15 hrs in a warm (35° C.) vacuum oven to produce 123.4 g (94.7%) 1-4 as an off-white solid.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with 1 L of water
  3. customThe precipitate was isolated by filtration
  4. customdried for 15 hrs in

Sources & evidence

ORD record
ord-4a21139022934614aaca272b8999f93e
Source dataset
uspto-grants-2010_06
Patent number
US07745657B2

Reaction notes

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