Triethylamine → N-Boc-glycyl-L-proline benzyl ester

HRID 1073988Notes

Reaction equation

HRID 1073988 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:14]([O:21][C:22](=[O:28])[C@@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:14]([O:21][C:22](=[O:28])[C@@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 13152016N-Boc-glycyl-L-proline benzyl esterYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-t-butyloxycarbonylglycine (21.02 g, 120 mmole), L-proline benzylester hydrochloride (29.01 g, 120 mmole) and HOBt (1.62 g, 12 mmole) were dissolved in methylene chloride (400 ml), and triethylamine (12.14 g, 120 mmole) and WSC hydrochloride (23.00 g, 120 mmole) were added to the solution at -30° C. The mixture 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 to give N-t-butyloxycarbonylglycyl-l-proline benzylester(yield 42.50 g, 97.7%).

Workup

  1. customovernight
  2. customat room temperature
  3. washThe solution was washed with 5% aqueous sodium bicarbonate (400 ml
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9a9a6bd7bae246d090c0f099e7f98c29
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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