Hydrochloric Acid → N-(cyclohexylglycyl-glutaminyl-serinyl)leucine benzyl ester hydrochloride

HRID 276770Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:41])[C@H:10]([CH2:37][CH:38]([CH3:40])[CH3:39])[NH:11][C:12](=[O:36])[C@H:13]([CH2:34][OH:35])[NH:14][C:15](=[O:33])[C@H:16]([CH2:28][CH2:29][C:30](=[O:32])[NH2:31])[NH:17][C:18](=[O:27])[CH2:19][NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:42].C(OCC)(=O)C>CO>[ClH:42].[CH2:1]([O:8][C:9](=[O:41])[C@H:10]([CH2:37][CH:38]([CH3:39])[CH3:40])[NH:11][C:12](=[O:36])[C@H:13]([CH2:34][OH:35])[NH:14][C:15](=[O:33])[C@H:16]([CH2:28][CH2:29][C:30](=[O:32])[NH2:31])[NH:17][C:18](=[O:27])[CH2:19][NH:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

The N-(cyclohexylglycyl-glutaminyl-serinyl)leucine benzyl ester (SEQ ID NO:3) hydrochloride (1.478 Kg) was slurried in methanol (14.8 L) at room temperature and the batch stirred for 1 hr. Ethyl acetate (29.6 L) was added over 30 minutes, the batch was cooled to 0-5° C. and aged for an hour. The solid collected by filtration, washed with cold (0-5° C.) methanol/ethyl acetate (4.5 L, 1:2), dried on the filter for 45 minutes, under nitrogen, and then dried under vacuum, at 40° C. This material was then utilized in subsequent reactions.

Workup

filtrationThe solid collected by filtration
washwashed with cold (0-5° C.) methanol/ethyl acetate (4.5 L, 1:2)
customdried on the
filtrationfilter for 45 minutes, under nitrogen
customdried under vacuum, at 40° C

Sources & evidence

ORD record: ord-ca8faab8868c49e2aa9819778b2a599b
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355611B1

Reaction notes

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