1,4-Dioxane hydrochloride → H-L-Ile-D-Pro-OBzl

HRID 2184656Notes

Reaction equation

HRID 2184656 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@@H:10]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].Cl.O1CCOCC1>O1CCOCC1>[NH2:1][C@H:2]([C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@@H:10]1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58726192HCID 58726192, compound

Product 1

HCID 58726083H-L-Ile-D-Pro-OBzlYield 101.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound Boc-L-Ile-D-Pro-OBzl (967 mg, 2.31 mmol) obtained in step 12-3 was dissolved in dioxane (12 ml) and 4N HCl/dioxane (12 ml) was added and the mixture was allowed to stand at room temperature for 1.5 hours. The reaction mixture was concentrated and diethyl ether/petroleum ether (1/3) was added to the residue followed by decantation to yield H-L-Ile-D-Pro-OBzl (745 mg, 91%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiethyl ether/petroleum ether (1/3) was added to the residue

Sources & evidence

ORD record
ord-a2d6ff7c07374a3f9238887371120b2a
Source dataset
uspto-grants-2002_06
Patent number
US06399568B1

Reaction notes

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