Sodium Hydroxide → Boc-Arg(Tos)-Pro-Ala-Lys(ClZ)-OH

HRID 723005Notes

Reaction equation

[NH:1]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C@H:2]([C:20]([N:22]1[CH2:61][CH2:60][CH2:59][C@H:23]1[C:24]([NH:26][C@H:27]([C:29]([NH:31][C@H:32]([C:49]([O:51]CC1C=CC=CC=1)=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][CH2:41][C:42]1[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=1[Cl:44])=[O:39])=[O:30])[CH3:28])=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[OH-].[Na+].C(Cl)(Cl)Cl.CO>CO>[NH:1]([C:62]([O:64][C:65]([CH3:66])([CH3:68])[CH3:67])=[O:63])[C@H:2]([C:20]([N:22]1[CH2:61][CH2:60][CH2:59][C@H:23]1[C:24]([NH:26][C@H:27]([C:29]([NH:31][C@H:32]([C:49]([OH:51])=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][CH2:41][C:42]1[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=1[Cl:44])=[O:39])=[O:30])[CH3:28])=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C. to the solution of 500 mg (0.51 mmol) of Boc-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12) in 5 ml of methanol 5 ml of the solution of NaOH in methanol (2 mol/L) were added. The reaction mixture was stirred at 0° C. for 2 h and TLC (chloroform/methanol, 15:1) indicated complete disappearance of Boc-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12). The reaction mixture was neutralized to pH 7 and evaporated at room temperature to remove methanol. The residue was acidified to pH 1–2 with hydrochloric acid (2 mol/L) to provide 380 mg (84%) of the title compound as a colorless powder. Mp 108–110° C., TOF-MS (m/e) 893.2[M+H]+, 915.5[M+Na]+, 937.2[M+2Na]+

Workup

customevaporated at room temperature
customto remove methanol

Sources & evidence

ORD record: ord-85c89ec0181d4eebaafb63f9f748d432
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138491B2

Reaction notes

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