5-Chlorothiophene-2-carbonyl Chloride → HCID 68486309, compound

HRID 2174713Notes

Reaction equation

HRID 2174713 reaction equation
[NH2:1][C:2]([CH2:8][O:9][CH3:10])([CH2:5][O:6][CH3:7])[CH2:3][OH:4].[Cl:11][C:12]1[S:16][C:15]([C:17](Cl)=[O:18])=[CH:14][CH:13]=1>C1COCC1>[OH:4][CH2:3][C:2]([NH:1][C:17]([C:15]1[S:16][C:12]([Cl:11])=[CH:13][CH:14]=1)=[O:18])([CH2:8][O:9][CH3:10])[CH2:5][O:6][CH3:7]

Participants

4

Reactant 2

HCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 20065886HCID 20065886, compound

Product 1

HCID 68486309HCID 68486309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.14 g (6.16 mmol) 2-amino-3-methoxy-2-methoxymethyl-propan-1-ol are suspended in 9 ml THF, cooled in the ice bath and combined with 2.56 ml (18.4 mmol) TEA. 1.12 g (6.19 mmol) 5-chlorothiophene-2-carboxylic acid chloride are dissolved in 6 ml THF and added dropwise. After 1.5 h the mixture is filtered and the filtrate is concentrated by evaporation i.vac. Then it is purified by chromatography through RP material (Microsorb C18 Varian; eluant:water/acetonitrile/trifluoroacetic acid=90:10:0.1=>0:100:0.1).

Workup

  1. additionadded dropwise
  2. filtrationAfter 1.5 h the mixture is filtered
  3. concentrationthe filtrate is concentrated by evaporation i.vac
  4. customThen it is purified by chromatography through RP material (Microsorb C18 Varian; eluant:water/acetonitrile/trifluoroacetic acid=90:10:0.1=>0:100:0.1)

Sources & evidence

ORD record
ord-5055c89641d44d53af30f4a20298fa35
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

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