Hydrochloric Acid → Leu-Pro-OBn

HRID 1393995Notes

Reaction equation

HRID 1393995 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])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.CCOC(C)=O>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])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10093486Boc-Leu-Pro-OBn

Product 1

HCID 10663366Leu-Pro-OBn

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flask containing Boc-Leu-Pro-OBn (113.8 g, 272 mmol) a solution of hydrogen chloride in dioxane (209 ml, 5.3 N) was added and the stirring was continued for 5 h or until total conversion by TLC (disappearance of starting material; Rf=0.47 (hex-EtOAc 2:1, silica). The solution was concentrated under reduced pressure and the resulting oil was chased with CHCl3 (3×50 ml), CHCl3-MTBE (30 ml-50 ml), MTBE (50 ml) and hex (50 ml). The residue was dried under vacuum (16 h) to remove residual HCl, to give the title compound as a white solid. A5 (96.4 g, 100%) was used directly without further purification in the next step. [α]D22−85.21 (c=1, CHCl3).

Workup

  1. additionwas added
  2. concentrationThe solution was concentrated under reduced pressure
  3. customThe residue was dried under vacuum (16 h)
  4. customto remove residual HCl

Sources & evidence

ORD record
ord-e8778ed70d4f4f88a012c9dab199b19b
Source dataset
uspto-grants-2008_03
Patent number
US07348310B2

Reaction notes

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