Sodium Hydroxide → HCID 178427540, compound

HRID 723003Notes

Reaction equation

[NH:1]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[C@H:2]([C:7]([NH:9][C@H:10]([C:28]([N:30]1[CH2:69][CH2:68][CH2:67][C@H:31]1[C:32]([NH:34][C@H:35]([C:37]([NH:39][C@H:40]([C:57]([O:59]CC1C=CC=CC=1)=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:46]([O:48][CH2:49][C:50]1[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=1[Cl:52])=[O:47])=[O:38])[CH3:36])=[O:33])=[O:29])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:27])[NH:16][S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[OH-].[Na+].C(Cl)(Cl)Cl.CO>CO>[NH:1]([C:70]([O:72][C:73]([CH3:74])([CH3:76])[CH3:75])=[O:71])[C@H:2]([C:7]([NH:9][C@H:10]([C:28]([N:30]1[CH2:69][CH2:68][CH2:67][C@H:31]1[C:32]([NH:34][C@H:35]([C:37]([NH:39][C@H:40]([C:57]([OH:59])=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:46]([O:48][CH2:49][C:50]1[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=1[Cl:52])=[O:47])=[O:38])[CH3:36])=[O:33])=[O:29])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:27])[NH:16][S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C. to the solution of 300 mg (0.210 mmol) of Boc-Asn-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 17) in 8 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-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 230 mg (83%) of the title compound as a colorless powder.

Workup

customevaporated at room temperature
customto remove methanol

Sources & evidence

ORD record: ord-6fd4c034aa7a497488c164965b5790bd
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138491B2

Reaction notes

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