Hydrochloric Acid → H-Lys(Z)-Leu-Leu-OMe.HCl

HRID 2298448Notes

Reaction equation

[ClH:1].[NH:2](C(OC(C)(C)C)=O)[C@H:3]([C:19]([NH:21][C@H:22]([C:27]([NH:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]>C(OCC)(=O)C>[NH2:2][C@H:3]([C:19]([NH:21][C@H:22]([C:27]([NH:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:28])[CH2:23][CH:24]([CH3:25])[CH3:26])=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10].[ClH:1]

Participants

Conditions

Temperature: -13.5 °C

Procedure

A solution of HCl (28 g, 770 mmol) in ethyl acetate (100 g) at −10° C. was rapidly added to Boc-Lys(Z)-Leu-Leu-OMe (35.0 g, 55.74 mmol) under N2 at −15 to −12° C. The mixture was stirred and maintained at −15 to −12° C. for 60 to 70 min and allowed to crystallize for 1 h at −10 to −5° C. The solid was filtered while excluding moisture, washed with several portions of t-butyl methyl ether and dried in vacuo to give H-Lys(Z)-Leu-Leu-OMe.HCl (28.7 g, 91.4%).

Workup

customto crystallize for 1 h at −10 to −5° C
filtrationThe solid was filtered
washwashed with several portions of t-butyl methyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-70cdc611cefb47b8ba57ce8a78322174
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492490B1

Reaction notes

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