Triethylamine → HCID 11826518, compound

HRID 1073999Notes

Reaction equation

HRID 1073999 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:21]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:21]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 11826518HCID 11826518, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-t-butyloxycarbonyl-L-phenylalanine (36.54 g, 137.7 mmole), L-proline benzylester hydrochloride (33.84 g, 140 mmole) and HOBT (18.91 g, 140 mmole) were dissolved in methylene chloride (500 ml), and triethylamine (14.17 g, 140 mmole) and WSC hydrochloride (26.40 g, 137.7 mmole) were added thereto at -30° C. The solution was stirred for 2 hours at less than 0° C. and then 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. The oily residue thus obtained was crystallized from ethyl acetate and n-hexane to give N-t-butyloxycarbonyl-L-phenylalanyl-L-proline benzylester (yield: 51.61 g, 82.8%).

Workup

  1. customat -30° C
  2. customovernight
  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. customThe oily residue thus obtained
  8. customwas crystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-5c29debb5a654dd18be44e8b22434fa7
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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