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

HRID 2298454Notes

Reaction equation

[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:34]([NH:36][C@H:37]([C:42]([NH:44][C@H:45]([C:50]([O:52][CH3:53])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[ClH:61]>CO>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:34]([NH:36][C@H:37]([C:42]([NH:44][C@H:45]([C:50]([O:52][CH3:53])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:38][CH:39]([CH3:40])[CH3:41])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[ClH:61]

Participants

Conditions

Temperature: 5 °C

Procedure

Boc-Leu-Leu-Lys(Z)-Leu-Leu-OMe (SEQ. ID No. 2) (18.2 g, 21.5 mmol) was added to a solution of HCl gas (31.0 g, 850 mmol) in MeOH (360 g) and cooled to 5° C. The reaction mixture was stirred, allowed to warm up to room temperature and stirring was continued for 4.5 h. The reaction mixture was cooled to 0° C., poured into ice/H2O (630 g) and stirred for 1 h. The white solid was collected by filtration, washed with distilled water (500 mL) and air dried. Yield of product: 14.8 g, 87.6%; HPLC area % purity: 99.2%.

Workup

temperatureto warm up to room temperature
stirringstirring
temperatureThe reaction mixture was cooled to 0° C.
stirringstirred for 1 h
filtrationThe white solid was collected by filtration
washwashed with distilled water (500 mL) and air
customdried

Sources & evidence

ORD record: ord-c01a1e4d9a3b4b5ca944ae132c920d72
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492490B1

Reaction notes

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