1,1'-(Diazomethylene)bis(benzene) → HCID 19778799, compound

HRID 2108082Notes

Reaction equation

[OH:1][CH:2]([CH:6]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]([OH:5])=[O:4].[C:33]1([C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[N+]=[N-])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[OH:1][CH:2]([CH:6]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]([O:5][CH:39]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:4]

Participants

Conditions

Temperature: 45 °C

Procedure

A partially dissolved mixture of 2-hydroxy-3-[(2-carboxyethyl)thio]-3-[2-(8-phenyloctyl)phenyl]propanoic acid prepared as in Example 20(c) (2.3 g, 5 mmol) in 25 ml of toluene was heated in an oil bath at 45° C. and stirred under argon while a solution of diphenyldiazomethane (1.02 g, 5.26 mmol) in 25 ml of toluene was added dropwise over a period of 20 minutes. The solvent was evaporated and the residue was flash chromatographed on silica gel (30% EtOAc/hexane, 1% HCO2H) to give the product.

Workup

additionwas added dropwise over a period of 20 minutes
customThe solvent was evaporated
customchromatographed on silica gel (30% EtOAc/hexane, 1% HCO2H)
customto give the product

Sources & evidence

ORD record: ord-2112a1b0d9b442199fc12e745b2f3c99
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04937253

Reaction notes

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