Acetic Anhydride → HCID 22178195, compound

HRID 900497Notes

Reaction equation

HRID 900497 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[Si:15]([CH2:22][CH2:23][CH:24]([OH:30])[C:25]([CH3:29])([CH3:28])[C:26]#[N:27])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C)C1C=CN=CC=1.CCOCC>[Si:15]([CH2:22][CH2:23][CH:24]([O:30][C:8](=[O:10])[CH3:9])[C:25]([CH3:29])([CH3:28])[C:26]#[N:27])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22178187HCID 22178187, compound2×

Product 1

HCID 22178195HCID 22178195, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

14.43 g (142.64 mmol) of triethylamine and 200 mg of 4-dimethylaminopyridine (DMAP), dissolved in 128 ml of MTB-ether, and, at 0° C., 14.56 g (142.64 mmol) of acetic acid anhydride are added to 28.24 g (109.7 mmol) of 5-tert-butyldimethylsilyl-2,2-dimethyl-3(R,S)-hydroxy-pentane-nitrile, the title compound of Example 6a, and it is stirred for 5 hours at room temperature. It is poured onto 2 l of ice water and extracted twice with 300 ml each of MTB-ether. The combined MTB-phases are washed once with 300 ml of 5% hydrochloric acid and then with water. It is evaporated to the dry state in a vacuum. The residue is purified by flash chromatography on silica gel (hexane/MTB-ether).

Workup

  1. extractionextracted twice with 300 ml each of MTB-ether
  2. washThe combined MTB-phases are washed once with 300 ml of 5% hydrochloric acid
  3. customIt is evaporated to the dry state in a vacuum
  4. customThe residue is purified by flash chromatography on silica gel (hexane/MTB-ether)

Sources & evidence

ORD record
ord-ed60b80ac4f940adae9a610e1efaa00f
Source dataset
uspto-grants-2008_04
Patent number
US07358382B2

Reaction notes

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