Acetic Anhydride → HCID 21891902, compound

HRID 1884064Notes

Reaction equation

HRID 1884064 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]([C:20]1[CH:36]=[C:35]2[N:23]([CH2:24][C:25]3[C:26]2=[N:27][C:28]2[C:33]([CH:34]=3)=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22](=[O:37])[C:21]=1[CH2:38][OH:39])([CH2:18][CH3:19])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C>ClCCl>[C:1]([O:39][CH2:38][C:21]1[C:22](=[O:37])[N:23]2[C:35](=[CH:36][C:20]=1[C:9]([OH:8])([CH2:18][CH3:19])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:26]1=[N:27][C:28]3[C:33]([CH:34]=[C:25]1[CH2:24]2)=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10646586HCID 10646586, compound

Product 1

HCID 21891902HCID 21891902, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (70 μl, 0.7 mmol) is added dropwise to a solution of tert-butyl 3-hydroxy-3-[8-(hydroxymethyl)-9-oxo-9,11-dihydroindolizino[1,2-b]quinolin-7-yl]pentanoate (200 mg, 0.46 mmol) and triethylamine (140 μl, 1 mmol) in dichloromethane (5 ml) and the resultant mixture is agitated at ambient temperature for 21 hours. The volatile components are evaporated off and the residue is purified by chromatography on a silica gel column (1-2% MeOH/CH2Cl2), which produces 152 mg of sought compound in the form of a yellow solid, m.p. 195-196° C.

Workup

  1. customThe volatile components are evaporated off
  2. customthe residue is purified by chromatography on a silica gel column (1-2% MeOH/CH2Cl2), which

Sources & evidence

ORD record
ord-e8e3aa014e3e4b47a22f8e1955ed1c68
Source dataset
uspto-grants-2004_07
Patent number
US06762301B2

Reaction notes

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