Hexamethylphosphoramide → HCID 59316845, compound

HRID 883637Notes

Reaction equation

HRID 883637 reaction equation
CC1SC(C2C=C(C)C=CC=2)=C(C(N2C(CN[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]4[O:26][C:25]([I:27])=[CH:24][C:23]=34)=[O:17])CSC2)=O)N=1.FC(F)(S(F)(=O)=O)C(OC)=[O:38].CN(P(N(C)C)(N(C)C)=O)C.CCOC(C)=O.CCCCCCC>CN(C=O)C.[Cu]I>[I:27][C:25]1[O:26][C:22]2[C:23](=[C:18]([C:16]([OH:17])=[O:38])[CH:19]=[CH:20][CH:21]=2)[CH:24]=1

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 547667Methyl 2,2-difluoro-2-(fluorosulfonyl)acetateHCID 21899848Ethylacetate heptaneHCID 86641457HCID 86641457, compound

Product 1

HCID 59316845HCID 59316845, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-iodo-benzofuran-4-carboxylic acid [3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-thiazolidin-4-ylmethyl]-amide (57 mg), copper (I) iodide (91 mg, 5 eq), methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (0.08 mL, 6.5 eq), HMPA (0.17 mL, 10 eq) in dry DMF (2.5 mL) was stirred at 80° C. for 16 hours under nitrogen. After cooling to rt, the reaction mixture was partitioned between water and EtOAc, the organic phase was washed again with water, dried (MgSO4), filtered and concentrated in vacuo to yield a crude yellow-orange oil. FC (AlO3, EtOAc/n-heptane: 7/3) gave the title compound (4.2 mg, 8%) as a white solid. LC-MS: tR=1.08 min; [m+H]+=546.22.

Workup

  1. temperatureAfter cooling to rt
  2. customthe reaction mixture was partitioned between water and EtOAc
  3. washthe organic phase was washed again with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a crude yellow-orange oil

Sources & evidence

ORD record
ord-57835b7a9e704cae894be0ed7e80891c
Source dataset
uspto-grants-2012_08
Patent number
US08236964B2

Reaction notes

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