Sodium Hydroxide → HCID 178427546, compound

HRID 723014Notes

Reaction equation

[NH:1]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:46][CH2:45][CH2:44][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([O:36]CC1C=CC=CC=1)=[O:35])[CH3:33])=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:5])[CH3:3].[OH-].[Na+].C(Cl)(Cl)Cl.CO.N(C(OC(C)(C)C)=O)[C@H](C(N[C@H](C(N1CCC[C@H]1C(N[C@H](C(N[C@H](C(OCC1C=CC=CC=1)=O)CCCCNC(OCC1C=CC=CC=1Cl)=O)=O)C)=O)=O)CCCNC(=N)NS(C1C=CC(C)=CC=1)(=O)=O)=O)CC(=O)N>CO>[NH:1]([C:47]([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48])[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:46][CH2:45][CH2:44][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([OH:36])=[O:35])[CH3:33])=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13][S:14]([C:17]1[CH:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=1)(=[O:16])=[O:15])=[O:5])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C. to the solution of 550 mg (0.726 mmol) of Boc-Ala-Arg(Tos)-Pro-Ala-OBzl (SEQ ID NO: 7) in 20 ml of methanol 8 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-Asn-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 17). 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 330 mg (67%) of the title compound as a colorless powder.

Workup

customevaporated at room temperature
customto remove methanol

Sources & evidence

ORD record: ord-c35342a4cc6842f89730164cb93d215a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138491B2

Reaction notes

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