1,2-Dichloroethane → HCID 86752458, compound

HRID 583711

Reaction equation

HRID 583711 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[CH:2].[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1.C([NH:25][CH2:26][C@H:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C:28]([OH:30])=[O:29])C.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH2:12]([O:30][C:28](=[O:29])[C@@H:27]([NH:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:34])[CH2:26][NH:25][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:11][CH:10]=1)[CH3:13]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 5897064-Ethynylbenzoic acidHCID 86752459Ethyl 2(S)-phenylsulfonylamino-beta-alanine p-toluenesulfonate

Product 1

HCID 86752458HCID 86752458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Ethynylbenzoic acid (35-1) (3.10 g, 21.2 mmol), 35-2 (8.58 g, 19.3 mmol), NMM (8.49 mL, 7.72 mmol), HOBT (3.39 g, 25.1 mmol), and EDC (4.81 g, 25.1 mmol) were combined in 96 mL DMF and stirred overnight. The reaction was concentrated, residue was diluted with EtOAc and washed with water (2×) and brine, dried (Na2SO4), filtered, and concentrated. Flash chromatography (silica, 45-50% EtOAc/Hexane) gave 35-3 as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additionresidue was diluted with EtOAc
  3. washwashed with water (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-268a8eabed7640b0a9ec915cc4429c22
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Linked notes

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