Sodium Hydroxide → HCID 178427544, compound

HRID 722999Notes

Reaction equation

HRID 722999 reaction equation
[NH:1]([C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:66][CH2:65][CH2:64][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([NH:36][C@H:37]([C:54]([O:56]CC1C=CC=CC=1)=[O:55])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][CH2:46][C:47]1[CH:53]=[CH:52][CH:51]=[CH:50][C:48]=1[Cl:49])=[O:44])=[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>CO>[NH:1]([C:67]([O:69][C:70]([CH3:72])([CH3:71])[CH3:73])=[O:68])[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:66][CH2:65][CH2:64][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([NH:36][C@H:37]([C:54]([OH:56])=[O:55])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][CH2:46][C:47]1[CH:53]=[CH:52][CH:51]=[CH:50][C:48]=1[Cl:49])=[O:44])=[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]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584188Chloroform methanolHCID 178427545HCID 178427545, compound

Product 1

HCID 178427544HCID 178427544, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C. to the solution of 100 mg (0.95 mmol) of Boc-Ala-Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 13) in 20 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-Ala-Arg(Tos)-Pro-Ala-Lys(ClZ)-Obzl (SEQ ID NO: 13). 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 880 mg (91%) of the title compound as a colorless powder.

Workup

  1. customevaporated at room temperature
  2. customto remove methanol

Sources & evidence

ORD record
ord-35ca5bff5def44818442fb43e4215df4
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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