Cesium carbonate → HCID 89699709, compound

HRID 1055650Notes

Reaction equation

HRID 1055650 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:17]([O:21][C:22](=[O:27])[NH:23][CH2:24][CH2:25]Br)([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CN(C=O)C.C(O)(=O)C>[C:17]([O:21][C:22]([NH:23][CH2:24][CH2:25][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:12])([F:13])([F:14])[F:15])[CH:10]=1)[C:5]([OH:7])=[O:6])=[O:27])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 581367943-Hydroxy-5-(pentafluorosulfanyl)benzoic acid

Product 1

HCID 89699709HCID 89699709, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

150 mg (0.57 mmol) of the compound of Example 24A, 140 mg (0.63 mmol) of tert-butyl-(2-bromoethyl)carbamate and 388 mg (1.2 mmol) of caesium carbonate were initially charged in 1.5 ml of DMF and stirred at RT overnight. 1.7 ml of 1 M aqueous sodium hydroxide solution were then added, and the mixture was stirred at RT for another 1 h. The reaction mixture was then acidified slightly with concentrated acetic acid and purified directly by preparative HPLC (Method 18). This gave 63 mg (26% of theory) of the title compound.

Workup

  1. stirringthe mixture was stirred at RT for another 1 h
  2. custompurified directly by preparative HPLC (Method 18)

Sources & evidence

ORD record
ord-0ae96bee0b86435b958935cd8d2501ea
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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