Ethyl Acetate → HCID 68542752, compound

HRID 1432095Notes

Reaction equation

HRID 1432095 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[N:14]=1)[C:9]([OH:11])=O)[CH2:2][CH:3]=[CH2:4].[C:17](OC(=O)N)(C)([CH3:19])[CH3:18].[CH:25]1[CH:26]=[CH:27][C:28]2N(O)N=[N:31][C:29]=2[CH:30]=1.CCN=C=N[CH2:40][CH2:41][CH2:42]N(C)C.Cl.CC[O:49][C:50](C)=[O:51]>CN(C=O)C.O>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[N:14]=1)[C:9]([NH:31][CH:29]([CH:28]1[CH2:27][CH:26]([CH3:25])[C:50](=[O:51])[O:49]1)[CH2:30][CH:41]([CH3:40])[CH2:42][CH2:19][CH:17]=[CH2:18])=[O:11])[CH2:2][CH:3]=[CH2:4]

Participants

8

Reactant 5

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 77922tert-Butyl carbamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68538578HCID 68538578, compound

Product 1

HCID 68542752HCID 68542752, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 155 mg (0.7 mmol) 2-but-3-enylamino-6-methoxy-isonicotinic acid (Acid IIIb), 105 mg (0.47 mmol) (R)-3-methyl-1-(4-methyl-5-oxo-tetrahydro-furan-2-yl)hept-6-enyl]-carbamic acid tert-butyl ester and 63 mg (0.42 mmol) HOBt.H2O in 8 ml DMF is cooled to 0°, treated with 107 mg (0.56 mmol) EDC.HCl and stirred at rt for 3 h. The reaction mixture is diluted with EtOAc and washed with 0.5 N aqueous citric acid, 2 M KHCO3 and brine, then dried over Na2SO4, filtered and evaporated. Chromatography on silica gel yields the title product as a colorless oil.

Workup

  1. washwashed with 0.5 N aqueous citric acid, 2 M KHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-b3e7484ac39244e3a0ff515d6bbc8544
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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