Hydrochloric Acid → BOC-Val-Pro-Pro-OBzl

HRID 1285361Notes

Reaction equation

[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].Cl.[NH:17]1[CH2:38][CH2:37][CH2:36][C@H:18]1[C:19]([N:21]1[CH2:35][CH2:34][CH2:33][C@H:22]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:20]>>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([N:17]1[CH2:38][CH2:37][CH2:36][C@H:18]1[C:19]([N:21]1[CH2:35][CH2:34][CH2:33][C@H:22]1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])=[O:20])=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 83693Boc-L-Valine

HCID 11130444Prolylproline benzyl ester

Product 1

HCID 13988140BOC-Val-Pro-Pro-OBzlYield 70%

Procedure

Starting from 13.79 g (63.45 mmol) of BOC-Val-OH and 21.5 g (63.45 mmol) of HCl.H-Pro-Pro-OBzl (VIII) and operating as described in Step 7, 22.28 g (70% yield) of compound IX were obtained as an oil after purification by column chromatography on silica gel (Merck) 0.040-0.063 mm eluting with ethyl acetate: methanol=98:2.

Sources & evidence

ORD record: ord-13859b8035754951bf8886f7d0d143b7
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04567162

Reaction notes

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