Water → HCID 15548879, compound

HRID 1815457Notes

Reaction equation

HRID 1815457 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:9].[C:20](=[O:58])([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[O:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([C@H:30]2[C@@H:42]3[C:43](=[O:46])[O:44][CH2:45][C@H:41]3[C@H:40]([OH:47])[C:39]3[C:31]2=[CH:32][C:33]2[O:37][CH2:36][O:35][C:34]=2[CH:38]=3)=[CH:24][C:23]=1[O:48][CH3:49].O>ClCCl>[C:8](=[O:9])([O:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[O:47][C@H:40]1[C@@H:41]2[CH2:45][O:44][C:43](=[O:46])[C@H:42]2[C@H:30]([C:25]2[CH:24]=[C:23]([O:48][CH3:49])[C:22]([O:21][C:20]([O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[O:58])=[C:27]([O:28][CH3:29])[CH:26]=2)[C:31]2[C:39]1=[CH:38][C:34]1[O:35][CH2:36][O:37][C:33]=1[CH:32]=2

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 13471176HCID 13471176, compound

Product 1

HCID 15548879HCID 15548879, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.155 ml of anhydrous pyridine is added to a solution of 1.71 mmol of p-nitrophenyl chloroformate in 5 ml of anhydrous dichloromethane. A white precipitate is formed in the reaction mixture. A solution of 0.502 mmol of the compound obtained in Step 1 in 5 ml of dichloromethane is then added dropwise under argon. Stirring is carried out for 45 minutes at ambient temperature, then 15 ml of water are poured into the reaction mixture. The organic phase is washed with water, dried over MgSO4, filtered and concentrated under recued pressure. Chromatography on silica gel (cyclohexane/ethyl acetate: 4/1) enables the expected product to be isolated.

Workup

  1. customA white precipitate is formed in the reaction mixture
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under recued pressure
  6. customto be isolated

Sources & evidence

ORD record
ord-0cb2fe7e94d14d96ae7145d763d7e22a
Source dataset
uspto-grants-2005_04
Patent number
US06878746B2

Reaction notes

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