Triethylamine → HCID 178501369, compound

HRID 2249978Notes

Reaction equation

HRID 2249978 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[CH:22]([C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31](Cl)=[O:32])[CH2:27][CH2:26]1)([CH3:24])[CH3:23]>ClCCl>[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:31]([C@H:28]1[CH2:29][CH2:30][C@H:25]([CH:22]([CH3:24])[CH3:23])[CH2:26][CH2:27]1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochlorideHCID 178448093HCID 178448093, compound

Product 1

HCID 178501369HCID 178501369, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

D-Phenylalanine methyl ester hydrochloride (26 g, 0.12 mol) was suspended in a solution of triethylamine (85 mL) in dichloromethane (125 mL) and the mixture was cooled to 0-5° C. A solution of trans-4-isopropylcyclohexane carbonyl chloride (25 g, 0.13 mol) in dichloromethane (75 mL) was added dropwise over a period of 10 minutes while maintaining the temperature at 0-5° C. The resulting mixture was stirred for 12 hours at ambient temperature then washed with 1.5 N HCl, 5% sodium bicarbonate solution and brine. The organic layer was concentrated to yield 38 g of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine methyl ester.

Workup

  1. temperaturewhile maintaining the temperature at 0-5° C
  2. washthen washed with 1.5 N HCl, 5% sodium bicarbonate solution and brine
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-3dbf887e73184911b3a641d2e50383c8
Source dataset
uspto-grants-2008_01
Patent number
US07314955B2

Reaction notes

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