Sodium Hydroxide → HCID 131726089, compound

HRID 723006Notes

Reaction equation

[N:1]1([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:40][CH2:39][CH2:38][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([NH:10][C@H:11]([C:28]([O:30]CC1C=CC=CC=1)=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[Cl:23])=[O:18])=[O:9])[CH3:7])=[O:4].[OH-].[Na+].C(Cl)(Cl)Cl.CO>CO>[N:1]1([C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])[CH2:40][CH2:39][CH2:38][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([NH:10][C@H:11]([C:28]([OH:30])=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[Cl:23])=[O:18])=[O:9])[CH3:7])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C. to the solution of 135 mg (0.2 mmol) of Boc-Pro-Ala-Lys(ClZ)-OBzl 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-Pro-Ala-Lys(ClZ)-OBzl. 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 100 mg (86%) of the title compound as a colorless powder.

Workup

customevaporated at room temperature
customto remove methanol

Sources & evidence

ORD record: ord-9c870da252ea42579fef6189f126e1d7
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138491B2

Reaction notes

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