Hydrochloric Acid → HCID 178485750, compound

HRID 1031748Notes

Reaction equation

HRID 1031748 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:21]([CH2:24][CH3:25])CC)C.C(Cl)(=O)O[CH2:28][CH3:29].Cl.[CH3:33][N:34](C)[CH:35]=[O:36]>O1CCCC1>[CH3:33][NH:34][C:35](=[O:36])[C@H:24]([CH2:25][C:29]1[CH:28]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:21][C:16]([C@H:13]1[CH2:12][CH2:11][C@H:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH2:14]1)=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 178453624HCID 178453624, compound

Product 1

HCID 178485750HCID 178485750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

On the other hand, trans-4-(t-butoxycarbonylaminomethyl)cyclohexyl carboxylic acid (203 g) was dissolved in dry tetrahydrofuran (80 ml) and triethylamine (1.19 ml) was added under ice-cooling to the solution, and the solution was stirred for 10 minutes. Subsequently, a solution of ethyl chlorocarbonate (0.85 g) in dry tetrahydrofuran (5 ml) was added and the mixture was further stirred for 20 minutes. The mixture was added to a mixture of the hydrochloride (II) previously obtained, triethylamine (1.19 ml), and N,N-dimethylformamide (5 ml) under ice-cooling, followed by stirring for 2 hours and again under room temperature for 2 hours. The solvent was evaporated under a reduced pressure, the residue was diluted with ice-water, and the precipitates were collected by filtration and washed with water. The product was washed with 10% aqueous citric acid and with water, followed by washing with 50% aqueous ethyl alcohol, 50% ethyl alcohol-ethyl ether, and dried to give N-[trans-4-(t-butoxycarbonylaminomethyl)cyclohexylcarbonyl]-L-phenylalanine methylamide (III) (2.57 g).

Workup

  1. temperaturecooling to the solution
  2. stirringthe mixture was further stirred for 20 minutes
  3. custompreviously obtained
  4. stirringby stirring for 2 hours and again under room temperature for 2 hours
  5. customThe solvent was evaporated under a reduced pressure
  6. additionthe residue was diluted with ice-water
  7. filtrationthe precipitates were collected by filtration
  8. washwashed with water
  9. washThe product was washed with 10% aqueous citric acid and with water
  10. washby washing with 50% aqueous ethyl alcohol, 50% ethyl alcohol-ethyl ether
  11. customdried

Sources & evidence

ORD record
ord-aed487cfb7e14ef8aff62a12f89f5f3f
Source dataset
uspto-grants-1990_09
Patent number
US04954512

Reaction notes

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