1-Hydroxybenzotriazole → Boc-Val-Pro-OBzl

HRID 1073992Notes

Reaction equation

HRID 1073992 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:17]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:17]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 14304307Boc-Val-Pro-OBzlYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-t-butyloxycarbonyl-L-valine (8.69 g, 40 mmole), L-proline benzylester hydrochloride (9.67 g, 40 mmole) and HOBt (5.40 g, 40 mmole) were dissolved in methylene chloride (150 ml), and N-methylmorcholine (4.05 g, 40 mmole) and WSC hydrochloride (7.67 g, 40 mmole) were added thereto at -30° C. The mixture was stirred for 2 hours at less than ° C., and then overnight at room temperature, washed with aqueous sodium bicarbonate (150 ml, twice), 5% aqueous citric acid (150 ml, twice) and water (150 ml) in the order given and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain N-t-butyloxycarbonyl-L-valyl-L-proline benzylester(yield: 16.32 g, 100%).

Workup

  1. customat -30° C
  2. wash, and then overnight at room temperature, washed with aqueous sodium bicarbonate (150 ml
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-07cd8bb500a8435fa69c8d5156764b94
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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