Triethylamine → HCID 14858901, compound

HRID 1074009Notes

Reaction equation

HRID 1074009 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:16]([O:23][C:24](=[O:30])[C@@H:25]1[CH2:29][CH2:28][CH2:27][NH:26]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:16]([O:23][C:24](=[O:30])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:12](=[O:14])[C@H:9]([CH2:10][OH:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 14858901HCID 14858901, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-t-butyloxycarbonyl-L-serine (33.86 g, 165 mmole), L-proline benzylester hydrochloride (39.88 g, 165 mmole) and HOBT (22.29 g, 165 mmole) were dissolved in methylene chloride (500 ml), and triethylamine (16.70 g, 5 mmole) and WSC hydrochloride (31.63 g, 165 mmole) were added thereto at -30° C. The mixture was stirred for 2 hours at less than 0° C., and next overnight at room temperature. The solution was washed with 5% aqueous sodium bicarbonate (400 ml, twice), 5% aqueous citric acid (400 ml, twice) and water (400 ml) in the order given, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to produce oily residue. The residue was crystallized from ethyl acetate and n-hexane to obtain N-t-butyloxycarbonyl-L-seryl-L-proline benzylester (yield: 36.09 g, 55.7%).

Workup

  1. customat -30° C
  2. customnext overnight
  3. customat room temperature
  4. washThe solution was washed with 5% aqueous sodium bicarbonate (400 ml
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto produce oily residue
  8. customThe residue was crystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-763a965315284d63a2ea427439b54b3b
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

Loading…