Dichloromethane → HCID 70237618, compound

HRID 651332Notes

Reaction equation

HRID 651332 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH2:5][CH3:6].[S:19]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20]1.Cl[CH2:28]Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(COC)OC>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([C:21]2[CH:22]=[CH:23][S:19][CH:20]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH:5]([CH3:28])[CH3:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acidHCID 70235390HCID 70235390, compound

Product 1

HCID 70237618HCID 70237618, compoundYield 1,273.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (2R)-(4-bromobenzenesulfonylamino)butyric acid methyl ester (9.911 g, 2.6 mmol), 3-thiopheneboronic acid (1.0 g, 7.81 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (1:1) (0.117 g, 0.14 mmol) and tribasic potassium phoshate (2.21 g, 10.4 mmol) in 20 mL of dimethoxyethane is heated at reflux for 16 h. The reaction is cooled and concentrated, and the residue is suspended in 100 mL of dichloromethane. The insolubles are removed by filtration and the filtrate is concentrated. Chromatography on silica gel (eluant; 1/9—EtOAc/hexane) affords 0.63 g (68%) of 3-methyl-(2R)-[4-(thiophen-3-yl)benzenesulfonylamino]butyric acid methyl ester.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 h
  3. temperatureThe reaction is cooled
  4. concentrationconcentrated
  5. customThe insolubles are removed by filtration
  6. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-b1db8a1566a3462d9fe8a584e7fdfb76
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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