Sodium Hydroxide → HCID 178427595, compound

HRID 723004Notes

Reaction equation

HRID 723004 reaction equation
[NH:1]([C:83]([O:85][C:86]([CH3:89])([CH3:88])[CH3:87])=[O:84])[C@H:2]([C:20]([NH:22][C@H:23]([C:41]([N:43]1[CH2:82][CH2:81][CH2:80][C@H:44]1[C:45]([NH:47][C@H:48]([C:50]([NH:52][C@H:53]([C:70]([O:72]CC1C=CC=CC=1)=[O:71])[CH2:54][CH2:55][CH2:56][CH2:57][NH:58][C:59]([O:61][CH2:62][C:63]1[CH:69]=[CH:68][CH:67]=[CH:66][C:64]=1[Cl:65])=[O:60])=[O:51])[CH3:49])=[O:46])=[O:42])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:40])[NH:29][S:30]([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31])=[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:83]([O:85][C:86]([CH3:87])([CH3:89])[CH3:88])=[O:84])[C@H:2]([C:20]([NH:22][C@H:23]([C:41]([N:43]1[CH2:82][CH2:81][CH2:80][C@H:44]1[C:45]([NH:47][C@H:48]([C:50]([NH:52][C@H:53]([C:70]([OH:72])=[O:71])[CH2:54][CH2:55][CH2:56][CH2:57][NH:58][C:59]([O:61][CH2:62][C:63]1[CH:69]=[CH:68][CH:67]=[CH:66][C:64]=1[Cl:65])=[O:60])=[O:51])[CH3:49])=[O:46])=[O:42])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:40])[NH:29][S:30]([C:33]1[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=1)(=[O:32])=[O:31])=[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:10])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584188Chloroform methanolHCID 178427596HCID 178427596, compound2×

Product 1

HCID 178427595HCID 178427595, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C. to the solution of 600 mg (0.464 mmol) of Boc-Arg(Tos)-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 18) in 10 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)-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 18). 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 420 mg (76%) of the title compound as a colorless powder.

Workup

  1. customevaporated at room temperature
  2. customto remove methanol

Sources & evidence

ORD record
ord-d6d47e23c81046a88524175693d3811b
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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