Anisole → HCID 178462178, compound

HRID 723015Notes

Reaction equation

HRID 723015 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:46][CH2:45][CH2:44][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([O:36]CC1C=CC=CC=1)=[O:35])[CH3:33])=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13]S(C1C=CC(C)=CC=1)(=O)=O)=[O:5])[CH3:3].C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:25]([N:27]1[CH2:46][CH2:45][CH2:44][C@H:28]1[C:29]([NH:31][C@H:32]([C:34]([OH:36])=[O:35])[CH3:33])=[O:30])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:13])[NH2:24])=[O:5])[CH3:3]

Participants

3

Reactant 2

HCID 7519AnisoleHCID 178427547HCID 178427547, compound

Product 1

HCID 178462178HCID 178462178, compoundYield 58.6%

Conditions

Temperature
0 °C

Procedure

The solution of 250 mg (0.330 mmol) of Boc-Ala-Arg(Tos)-Pro-Ala-OBzl (SEQ ID NO: 7), 1 ml of anisole and 2 ml of HF was stirred at 0° C. for 2 h. The reaction mixture was evaporated under reduced pressure to remove HF. To the residue 2 ml of HF were added and the solution was stirred at 0° C. for another 1 h. The reaction mixture was evaporated under reduced pressure to remove HF. The residue was triturated with ether and the resulted solid was purified on the Sephadex G-10 column. The collected fractions were lyophilized to provide 80 mg (58%) of the title compound. Mp. 157–159° C., FAB-MS (m/e) 415[M+H]+.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto remove HF
  3. additionTo the residue 2 ml of HF were added
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customto remove HF
  6. customThe residue was triturated with ether
  7. customthe resulted solid was purified on the Sephadex G-10 column

Sources & evidence

ORD record
ord-fb287360229e4c26b33918a7e884cf46
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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