Diisopropylethylamine → HCID 50919249, compound

HRID 1851895Notes

Reaction equation

HRID 1851895 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]4[C:32]([C:37]([O:39]C(C)(C)C)=[O:38])=[CH:33][CH:34]=[CH:35][CH:36]=4)=[CH:27][CH:26]=2)[CH:19]=[CH:18]3)=[O:14])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C>CCCCCC.CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]4[C:32]([C:37]([OH:39])=[O:38])=[CH:33][CH:34]=[CH:35][CH:36]=4)=[CH:27][CH:26]=2)[CH:19]=[CH:18]3)=[O:14])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 50919247HCID 50919247, compound

Product 1

HCID 50919249HCID 50919249, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of (S)-tert-butyl 4′-((5-((1-(4-nitrophenyl)ethyl)carbamoyl)-1H-indol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylate (23 mg, 0.04 mmol, 1 equiv) in DCM/TFA 1/1 was stirred for 30 min at room temperature. The reaction mixture was neutralized by addition of DIEA, concentrated and purified by preparative HPLC to afford a beige powder (9 mg, 0.02 mmol, 43%). ESI-MS (m/z): 520 [M+H]+.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8b8319175b144136a8b28dee0f1e47a1
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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