Dimethylformamide → HCID 3625286, compound

HRID 2351823Notes

Reaction equation

HRID 2351823 reaction equation
C[N:2]([CH3:5])C=O.[CH2:6](N(CC)CC)C.[C:13](Cl)(=[O:17])[O:14]CC.Br[C:20]1[CH:21]=[CH:22][C:23]([O:26][C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30](O)=O)=N[CH:25]=1>O1CCCC1>[O:26]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[CH2:30][CH:5]([C:13]([OH:17])=[O:14])[NH2:2])[C:23]1[CH:22]=[CH:21][CH:20]=[CH:25][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 198462343-(5-Bromo-2pyridyloxy)benzoic acid

Product 1

HCID 3625286HCID 3625286, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

On the other hand, trans-4-(t-butoxycarbonyl)aminomethylcyclohexylcarbonxylic acid (1.62 g) was dissolved in dry tetrahydrofuran (50 ml) and dry N,N-dimethylformamide (20 ml), triethylamine (0.96 ml) was added to the resultant solution and a solution of ethyl chlorocarbonate (0.76 g) in tetrahydrofuran (2 ml) was added to the mixture under ice-cooling, followed by stirring for 30 minutes. To this solution was added the hydrochloride (III) previously obtained and triethylamine (2 ml) was added to the mixture, followed by stirring at room temperature for 3 hours. Ice-water (200 ml) was added to the reaction mixture and the precipitated crystalline substance was collected by filtration, thoroughly washed with water and dried to obtain 2.62 g of N-[trans-4(t-butyloxycarbonyl)aminomethylcyclohexylcarbonyl]-3-phenoxy-DL-phenylalanine 4-acetylanilide (IV) in the form of a white powder. The compound (IV) was confirmed by an NMR analysis.

Workup

  1. temperaturecooling
  2. custompreviously obtained
  3. stirringby stirring at room temperature for 3 hours
  4. filtrationthe precipitated crystalline substance was collected by filtration
  5. washthoroughly washed with water
  6. customdried

Sources & evidence

ORD record
ord-443d958d57974a7aa7012cb0d2cf4354
Source dataset
uspto-grants-1989_10
Patent number
US04873253

Reaction notes

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