Anisole → HCID 178462134, compound

HRID 722997Notes

Reaction equation

HRID 722997 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:20]([N:22]1[CH2:61][CH2:60][CH2:59][C@H:23]1[C:24]([NH:26][C@H:27]([C:29]([NH:31][C@H:32]([C:49]([O:51]CC1C=CC=CC=1)=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37]C(OCC1C=CC=CC=1Cl)=O)=[O:30])[CH3:28])=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8]S(C1C=CC(C)=CC=1)(=O)=O.C1(OC)C=CC=CC=1>>[NH2:1][C@H:2]([C:20]([N:22]1[CH2:61][CH2:60][CH2:59][C@H:23]1[C:24]([NH:26][C@H:27]([C:29]([NH:31][C@H:32]([C:49]([OH:51])=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][NH2:37])=[O:30])[CH3:28])=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:19]

Participants

3

Reactant 2

HCID 7519AnisoleHCID 178427588HCID 178427588, compound

Product 1

HCID 178462134HCID 178462134, compoundYield 84%

Conditions

Temperature
0 °C

Procedure

The solution of 280 mg (0.285 mmol) of Boc-Arg(Tos)-Pro-Ala-Lys(ClZ)OBzl (SEQ ID NO: 12), 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 110 mg (84%) of the title compound. Mp. 158–160° C., FAB-MS (m/e) 472[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-da2f074a106b4cd39248bb82fab5b668
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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