Oxalyl chloride → HCID 15105970, compound

HRID 703702Notes

Reaction equation

HRID 703702 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH2:8][S:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([N:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)(=O)C(Cl)=O>C(N(CC)CC)C>[C:19]([C:16]1[CH:15]=[C:7]([CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:17]=1[OH:18])[CH2:8][S:9][CH2:10][CH2:11][C:12]([O:14][N:30]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:13])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 69297DibenzylhydroxylamineHCID 15135146HCID 15135146, compound

Product 1

HCID 15105970HCID 15105970, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The compound is prepared using the method of Example II, with 16.20 g of 3-(3,5-di-tert-butyl-4-hydroxybenzylthio)propanoic acid, 10.66 g of N,N-dibenzylhydroxylamine, 5.06 g of triethylamine, and 6.35 g of oxalyl chloride. The residue is purified by preparative HPLC to give 3.0 g of a white solid: mp 84°-86° C.

Workup

  1. customThe compound is prepared
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-78bdb429a1f9456e8efae57e4420b85f
Source dataset
uspto-grants-1991_01
Patent number
US04983770

Reaction notes

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