Propionic Acid → HCID 66896471, compound

HRID 337591Notes

Reaction equation

HRID 337591 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][NH2:20])[CH:5]=[C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:7]=1[Cl:8].CCN(C(C)C)C(C)C.[C:30](O)(=[O:33])[CH2:31][CH3:32].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CCOCC.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][NH:20][C:30](=[O:33])[CH2:31][CH3:32])[CH:5]=[C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:12])[CH3:13])[C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66895829HCID 66895829, compound

Product 1

HCID 66896471HCID 66896471, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a DMF (0.2 M) solution of 2-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)-silyl]oxy}methyl)phenyl]ethanamine (1 eq.) from the previous step, Hunig's base (3 eq.) and propionic acid (1.1 eq.) was added portionwise O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.2 eq.). The resulting reaction solution was stirred at RT for 48 h. The now reddish solution was diluted with ether and washed sequentially with 1 N aq. NaOH, water and brine. The organic extract was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe resulting reaction solution
  2. washwashed sequentially with 1 N aq. NaOH, water and brine
  3. extractionThe organic extract
  4. dry with materialwas then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto afford a brown oil
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-46d3e80e818346af9c887a82feb5c770
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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