Acetic Anhydride → HCID 22178190, compound

HRID 900492Notes

Reaction equation

HRID 900492 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:15][CH2:16][CH2:17][CH:18]([OH:24])[C:19]([CH3:23])([CH3:22])[C:20]#[N:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CCOCC>[CH2:8]([O:15][CH2:16][CH2:17][CH:18]([O:24][C:1](=[O:3])[CH3:2])[C:19]([CH3:22])([CH3:23])[C:20]#[N:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22178189HCID 22178189, compound2×

Product 1

HCID 22178190HCID 22178190, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

14.56 g (42.64 mmol) of acetic acid anhydride is added at 0° C. to a solution that consists of 25.6 g (109.7 mmol) of 5-benzyloxy-2,2-dimethyl-3-hydroxy-pentane-nitrile of the title compound of Example 1a, 14.43 g (142.64 mmol) of triethylamine and 200 mg of 4-dimethylaminopyridine (DMAP), dissolved in 128 ml of MTB-ether, and it is stirred for 5 hours at room temperature. The reaction mixture 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.

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

Sources & evidence

ORD record
ord-ac96efd5757c429383b1fb6a09c8bbc9
Source dataset
uspto-grants-2008_04
Patent number
US07358382B2

Reaction notes

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