Acetic Anhydride → HCID 69981834, compound

HRID 1935626Notes

Reaction equation

HRID 1935626 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]3[CH2:24][CH:23]([CH2:25][NH2:26])[O:22][C:21]3=[O:27])=[CH:17][CH:18]=2)[CH2:13][CH:12]1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:37](=[O:39])[CH3:38])[O:22][C:21]3=[O:27])=[CH:17][CH:18]=2)[CH2:13][CH:12]1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22464027HCID 22464027, compound

Product 1

HCID 69981834HCID 69981834, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An ice cold, stirred mixture of the product from Step 7 (6.39 g, 0.0125 mol) and pyridine (75 ml), under nitrogen is treated, dropwise during 10 min, with acetic anhydride (24 ml). The mixture is kept in the ice bath for 20 min and at ambient temperature for 2 h. It is then concentrated in vacuo. The residue is mixed with ethyl acetate, washed with dilute sodium bicarbonate, water, and brine, dried (Na2SO4) and concentrated. Chromatography of the residue on silica gel with mixtures of MeOH—CH2Cl2 containing 2.5 −5% MeOH gave the titled product: MS (ES) m/z 554 (M+H+), 576 (M+Na+); 1H NMR (300 MHz, CDCl3) δ−0.12 (s, 3H), −0.07 (s, 3H), 0.75 (s, 9H), 2.01 (s, 3H), 3.08 (m, 1H), 3.23 (m, 1H), 3.58 (m, 2H), 3.73 (m, 3H), 4.00 (m, 1H), 4.50 (broad s, 1H), 4.73 (m, 1H), 5.27 (m, 2H), 6.22 (broad s, 1H), 7.08 (m, 1H), 7.37 (m, 6H), 7.79 (broad s, 1H).

Workup

  1. concentrationIt is then concentrated in vacuo
  2. additionThe residue is mixed with ethyl acetate
  3. washwashed with dilute sodium bicarbonate, water, and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6b0af4db4b4d49f7950e5931051e4ddd
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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