Triethylamine → HCID 178453621, compound

HRID 1031744Notes

Reaction equation

HRID 1031744 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(CC)CC)C.C(Cl)(=O)OCC.Cl.[NH2:33][C@H:34]([C:42]([NH2:44])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]([NH:44][C:42](=[O:43])[C@H:34]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH2:33])=[O:18])[CH2:14][CH2:15]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 11953719L-Phenylalaninamide hydrochlorideHCID 178453624HCID 178453624, compound

Product 1

HCID 178453621HCID 178453621, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trans-4-(t-butoxycarbonylaminomethyl)cyclohexyl carboxylic acid (3.86 g) dissolved in dry tetrahydrofuran (150.00 ml), triethylamine (2.25 ml) was added under ice-cooling and the mixture was stirred for 5 minutes. A solution of ethyl chlorocarbonate (1.63 g) in dry tetrahydrofuran (10.00 ml) was added to the mixture under ice-cooling, and the mixture was stirred at the same temperature for 20 minutes. L-phenylalanine amide hydrochloride and triethylamine (2.25 ml) were added to the mixture, and the mixture was stirred under ice-cooling for 2 hours and under room temperature for one hour, followed by concentration under a reduced pressure. Water was added to the residue, and the insolubles therein were filtered, thoroughly washed with water, and further washed with 50% aqueous ethyl alcohol and 50% ethyl alcohol-ethyl ether, followed by drying, to give N-[trans-4-(t-butoxycarbonylaminomethyl)cyclohexylcarbonyl]-L-phenylalanine amide (I) (4.82 g) as a white powder. This structure was confirmed by NMR spectrum.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 20 minutes
  4. stirringthe mixture was stirred under ice-
  5. concentrationfollowed by concentration under a reduced pressure
  6. additionWater was added to the residue
  7. filtrationthe insolubles therein were filtered
  8. washthoroughly washed with water
  9. washfurther washed with 50% aqueous ethyl alcohol and 50% ethyl alcohol-ethyl ether
  10. customby drying

Sources & evidence

ORD record
ord-19be8c3859f540dc9419045ce65e0de5
Source dataset
uspto-grants-1990_09
Patent number
US04954512

Reaction notes

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