Water → HCID 68284522, compound

HRID 1527193Notes

Reaction equation

HRID 1527193 reaction equation
[Br-].[CH2:2]([O:9][C:10]([CH2:12][N+:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[C:20]#[CH:21].C(N(CC)CC)C.O>CN(C=O)C>[C:24]([O:23][C:19]([C:20]1[CH:21]=[C:12]([C:10]([O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:11])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 543038tert-Butyl propiolateHCID 85615786HCID 85615786, compound

Product 1

HCID 68284522HCID 68284522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 1-benzyloxycarbonylmethyl-pyridinium bromide (1.50 g, 9.74 mmol) and tert-butyl propiolate (1.34 mL, 9.74 mmol) in DMF (80 mL) was added a solution of triethylamine (4.1 mL, 29.2 mmol) in DMF (10 mL). The mixture was vigourously stirred 4 h at 60° C. under air atmosphere. The solution was allowed to cool to RT, poured into water and extracted with EtOAc (2×). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 8:2) to give the desired material. TLC, Rf (c-hexane/EtOAc 8:2)=0.6; MS (LC/MS): 725.3 [2M+Na]+; tR (HPLC conditions a): 4.84 min.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 8:2)

Sources & evidence

ORD record
ord-a39ef37ebd8648af96477fa3a7b2e7fd
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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