Sodium Hydroxide → HCID 178427538, compound

HRID 723002Notes

Reaction equation

[NH:1]([C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])[C@H:2]([C:8]([NH:10][C@H:11]([C:29]([N:31]1[CH2:70][CH2:69][CH2:68][C@H:32]1[C:33]([NH:35][C@H:36]([C:38]([NH:40][C@H:41]([C:58]([O:60]CC1C=CC=CC=1)=[O:59])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][CH2:50][C:51]1[CH:57]=[CH:56][CH:55]=[CH:54][C:52]=1[Cl:53])=[O:48])=[O:39])[CH3:37])=[O:34])=[O:30])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:28])[NH:17][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[OH-].[Na+].C(Cl)(Cl)Cl.CO>CO>[NH:1]([C:71]([O:73][C:74]([CH3:75])([CH3:77])[CH3:76])=[O:72])[C@H:2]([C:8]([NH:10][C@H:11]([C:29]([N:31]1[CH2:70][CH2:69][CH2:68][C@H:32]1[C:33]([NH:35][C@H:36]([C:38]([NH:40][C@H:41]([C:58]([OH:60])=[O:59])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][CH2:50][C:51]1[CH:57]=[CH:56][CH:55]=[CH:54][C:52]=1[Cl:53])=[O:48])=[O:39])[CH3:37])=[O:34])=[O:30])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:28])[NH:17][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C. to the solution of 770 mg (0.694 mmol) of Boc-Gln-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 16) in 18 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-Gln-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 16). 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 610 mg (86%) of the title compound as a colorless powder.

Workup

customevaporated at room temperature
customto remove methanol

Sources & evidence

ORD record: ord-19c7dc129e714945999dbbd3160dfb6c
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138491B2

Reaction notes

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