1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Benzyloxycarbonylamino-4-(1-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-butyric acid ethyl ester

HRID 2088332Notes

Reaction equation

HRID 2088332 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:6][CH2:7][C:8]([OH:10])=O)[CH3:2].CCN=C=NCCCN(C)C.[CH2:34]([O:36][C:37](=[O:42])[C@H:38]([CH2:40][OH:41])[NH2:39])[CH3:35]>C(#N)C>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:6][CH2:7][C:8](=[O:10])[NH:39][CH:38]([C:37]([O:36][CH2:34][CH3:35])=[O:42])[CH2:40][OH:41])[CH3:2]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2924245-Ethoxy-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acidHCID 2724186Ethyl serinate

Product 1

HCID 687324842-Benzyloxycarbonylamino-4-(1-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-butyric acid ethyl esterYield 118.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of acid (3) (7.6 g, 24.57 mmol) in dry acetonitrile (80 ml) was stirred under nitrogen at room temperature and Hobt (4 g, 29.6 mmol, 1.2 equiv.) was added. Stirring was continued for 10 min., and EDCI (5.1 g, 26.6 mmol, 1.1 equiv.) was added. The resulting mixture was stirred for 1.5 hrs and serine ethyl ester free base (3.27 g, 24.57 mmol, 1 equiv.) in acetonitrile (20 ml) was added. Stirring was continued at room temperature for 3 hrs. The solvent was removed in a rotary evaporator, the residue was partitioned between water (100 ml) and ethyl acetate (200 ml) and phases were separated. The organic phase was washed successively with water (50 ml), 5% potassium carbonate (2×50 ml) and water (2×50 ml), dried over sodium sulfate and the solvent removed in a rotary evaporator. The residue was dried in a vacuum oven (50° C.) to produce (4) (12.4 g, 85.5%).

Workup

  1. additionHobt (4 g, 29.6 mmol, 1.2 equiv.) was added
  2. stirringStirring
  3. stirringThe resulting mixture was stirred for 1.5 hrs
  4. stirringStirring
  5. waitwas continued at room temperature for 3 hrs
  6. customThe solvent was removed in a rotary evaporator
  7. customthe residue was partitioned between water (100 ml) and ethyl acetate (200 ml) and phases
  8. customwere separated
  9. washThe organic phase was washed successively with water (50 ml), 5% potassium carbonate (2×50 ml) and water (2×50 ml)
  10. dry with materialdried over sodium sulfate
  11. customthe solvent removed in a rotary evaporator
  12. customThe residue was dried in a vacuum oven (50° C.)

Sources & evidence

ORD record
ord-b76c1db191134abf843930f1df879385
Source dataset
uspto-grants-2013_05
Patent number
US08435956B2

Reaction notes

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