Methanol → HCID 67237126, compound

HRID 1985720Notes

Reaction equation

HRID 1985720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][OH:23])=[C:14](Br)[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C]=O.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C.[CH3:63][OH:64]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]2[N:18]([C:17]3[N:16]=[C:15]4[CH2:22][O:23][C:63](=[O:64])[C:14]4=[CH:13][C:12]=3[CH2:11]2)[C@H:19]([CH3:21])[CH2:20]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 67238425HCID 67238425, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 67237126HCID 67237126, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The product of step 1 was carbonylated in methanol with carbon monoxide (35 bar) at 110° C. (24 h) in the presence of palladium acetate (0.02 eq), dppp (0.025 eq) and triethylamine (3 eq). The solvent was evaporated and the residue was purified by chromatography on silica gel with ethyl acetate:heptane to yield the title compound as with crystals (MS: 346.3 (M+H+))

Workup

  1. custom(24 h)
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-ae169ecc79224e81a52eb70432b74a07
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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