Ethanol → HCID 53988496, compound

HRID 412856Notes

Reaction equation

HRID 412856 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:15][C@H:16]1[C@H:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:29]([CH2:39][OH:40])[O:28][C@@H:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C@@H:17]1[N:41]1[C:45](=[O:46])[C:44]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]2[C:42]1=[O:51])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:1]([O:40][CH2:39][C@H:29]1[O:28][C@@H:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C@H:17]([N:41]2[C:42](=[O:51])[C:43]3=[CH:50][CH:49]=[CH:48][CH:47]=[C:44]3[C:45]2=[O:46])[C@@H:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:30]1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 54035589HCID 54035589, compound

Product 1

HCID 53988496HCID 53988496, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Under nitrogen gas atmosphere, acetic anhydride (200 ml) and DMAP (catalytic amount) were added to a solution of Compound 21 (10.5 g, 17.6 mmol) in pyridine (200 ml), and the mixture was stirred for 20 hours. Ethanol was added to the reaction mixture, and it was stirred for 20 minutes. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=4:1) to obtain Compound 22 (9.6 g, 85%).

Workup

  1. stirringwas stirred for 20 minutes
  2. customThe solvent was then evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c225423c19a14ce1a90c2666d3ef2591
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

Loading…