Dimethylformamide → HCID 976170, compound

HRID 1005599Notes

Reaction equation

HRID 1005599 reaction equation
[C:1](OC(NCC(O)=O)=O)([CH3:4])([CH3:3])C.Cl.C(N=C=N[CH2:19][CH2:20][CH2:21]N(C)C)C.O[C:26]1[C:34]2N=NN[C:30]=2[CH:29]=[CH:28][CH:27]=1.[CH3:35][N:36](C)[CH:37]=[O:38]>C(OCC)(=O)C>[C:26]1([C:3]2[CH:1]=[CH:4][CH:21]=[CH:20][C:19]=2[C:37]([NH:36][CH3:35])=[O:38])[CH:34]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 976170HCID 976170, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-methoxy-4-[2-[3-(tert-butoxycarbonyl)aminoprop-1-yl]oxybenzoyl]amino-N-[2-(4-aminobut-1-yl)oxy-4-methyl]phenyl-N-methylbenzamide (365 mg) and N-(tert-butoxycarbonyl)glycine (111 mg) in N,N-dimethylformamide (15 ml) were added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (132 mg) and hydroxybenzotriazole (93.2 mg) and the mixture was stirred at ambient temperature overnight. The solution was diluted with ethyl acetate (30 ml) and the solution was washed successively with saturated aqueous sodium hydrogen carbonate, water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an amorphous. The crude product was purified by silica gel column chromatography (1% methanol in chloroform) to give 3-methoxy-4-[2-[3-tert-butoxycarbonyl)aminoprop-1-yl]oxybenzoyl]amino-N-[2-4-(tert-butoxycarbonylamino)acetylaminobut-1-yl)oxy-4-methyl]phenyl-N-methylbenzamide (320 mg).

Workup

  1. washthe solution was washed successively with saturated aqueous sodium hydrogen carbonate, water and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customto give an amorphous
  5. customThe crude product was purified by silica gel column chromatography (1% methanol in chloroform)

Sources & evidence

ORD record
ord-bbdadaee03464d1286ad63e784702a4e
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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