Toluene → HCID 86758969, compound

HRID 412867Notes

Reaction equation

HRID 412867 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:42]([OH:43])[C@@H:41]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:40]([CH2:52][O:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[O:39][C@H:10]1[O:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][C@H:18]([C@@H:20]1[C@:37]2([CH3:38])[C@H:23]([C@H:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[CH:27]([CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:26][CH2:25]3)[CH2:22][CH2:21]1)[CH3:19])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:60](OC(=O)C)(=[O:62])[CH3:61].C1(C)C=CC=CC=1>N1C=CC=CC=1>[C:60]([O:43][C@H:42]1[C@@H:41]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:40]([CH2:52][O:53][C:54](=[O:59])[C:55]([CH3:57])([CH3:56])[CH3:58])[O:39][C@@H:10]([O:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][C@H:18]([C@@H:20]2[C@:37]3([CH3:38])[C@H:23]([C@H:24]4[C@H:34]([CH2:35][CH2:36]3)[C@:32]3([CH3:33])[CH:27]([CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:26][CH2:25]4)[CH2:22][CH2:21]2)[CH3:19])[CH3:14])[C@@H:9]1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:62])[CH3:61]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 86758967HCID 86758967, compound

Product 1

HCID 86758969HCID 86758969, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 27 (10 mg, 12.3 μmol) was dissolved in pyridine (1 mL). To the solution, acetic anhydride (0.5 mL) was added, and the mixture was stirred at the room temperature for 1 hour. The solvent was subjected to azeotropy with toluene, and the residue was purified with Sephadex LH-20 (CHCl3:MeOH=1:2) to obtain Compound 28 (9 mg, 85.4%).

Workup

  1. customthe residue was purified with Sephadex

Sources & evidence

ORD record
ord-7b7fcaca20e7430b872143b1d1cebbc5
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

Loading…