Boc-prolylproline benzyl ester → Isopropanol ethyl acetate

HRID 1285360Notes

Reaction equation

HRID 1285360 reaction equation
[N:1]1(C([O:25][C:26](C)([CH3:28])[CH3:27])=O)[CH2:22][CH2:21][CH2:20][C@H:2]1[C:3]([N:5]1[CH2:19][CH2:18][CH2:17][C@H:6]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4]>Cl.C(O)(=O)C>[NH:1]1[CH2:22][CH2:21][CH2:20][C@H:2]1[C:3]([N:5]1[CH2:19][CH2:18][CH2:17][C@H:6]1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])=[O:4].[CH3:27][CH:26]([OH:25])[CH3:28].[CH3:11][CH2:10][O:9][C:7]([CH3:6])=[O:8]

Participants

5

Reactant 1

HCID 13091041Boc-prolylproline benzyl ester

Product 2

HCID 11130444Prolylproline benzyl esterHCID 22055037Isopropanol ethyl acetateYield 342.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

34.21 g (85 mmol) of BOC-Pro-Pro-OBzl (VII) were dissolved in 342 ml of a saturated solution of hydrogen chloride in acetic acid at room temperature. After 30 minutes BOC-removal was complete and the solvent was removed in vacuo. From iPrOH/AcOEt 21.60 g (75% yield) of compund VIII were obtained: RfD 0.32; E1.2 1.12.

Workup

  1. customAfter 30 minutes BOC-removal
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-504ee13f7113462ab7aece77b6320a16
Source dataset
uspto-grants-1986_01
Patent number
US04567162

Reaction notes

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