Dichloromethane → HCID 20464124, compound

HRID 325790Notes

Reaction equation

HRID 325790 reaction equation
[C:1]([O:7][C:8]1[CH:42]=[CH:41][C:11]([C:12]([O:14][C:15]2[CH:16]=[C:17]([CH:37]([OH:40])[CH2:38]Br)[CH:18]=[C:19]([O:21][C:22](=[O:36])[C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:25][CH:24]=3)[CH:20]=2)=[O:13])=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:43]([NH2:47])([CH3:46])([CH3:45])[CH3:44].C(Cl)[Cl:49]>>[ClH:49].[C:1]([O:7][C:8]1[CH:42]=[CH:41][C:11]([C:12]([O:14][C:15]2[CH:16]=[C:17]([CH:37]([OH:40])[CH2:38][NH:47][C:43]([CH3:46])([CH3:45])[CH3:44])[CH:18]=[C:19]([O:21][C:22](=[O:36])[C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:25][CH:24]=3)[CH:20]=2)=[O:13])=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 20464113HCID 20464113, compound

Product 1

HCID 20464124HCID 20464124, compound

Procedure

A solution of 3.2 g (0.005 moles) of 1-[3',5'-bis-(4-pivaloyloxybenzoyloxy)phenyl]-2-bromoethanol and 1.1 g (0.015 moles) of t-butylamine in 100 ml of methylene chloride was boiled under reflux for 18 hrs. After evaporation to dryness, diethyl ether was added to the residue. The precipitated t-butylamino hydrobromide (0.2 g) was filtered off and the filtrate was then acidified with ethanolic hydrochloric acid. HPLC analysis of this solution showed the presence of the title compound as compared with an authentic sample. ##STR63## The 1-[3',5'-bis-(4-pivaloyloxybenzoyloxy)phenyl]-2-bromoethanol which was used as starting material was prepared as follows.

Workup

  1. temperatureunder reflux for 18 hrs
  2. customAfter evaporation to dryness, diethyl ether
  3. additionwas added to the residue
  4. filtrationThe precipitated t-butylamino hydrobromide (0.2 g) was filtered off
  5. customwas prepared

Sources & evidence

ORD record
ord-e343f41f61ce476f9e80c3ea7ef0b3cb
Source dataset
uspto-grants-1984_04
Patent number
US04442300

Reaction notes

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