1-Hydroxybenzotriazole → HCID 178454176, compound

HRID 615275Notes

Reaction equation

HRID 615275 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:19]([OH:21])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[Cl:14])=[O:9].[NH2:29][C@H:30]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[NH:40])[NH:36][N+:37]([O-:39])=[O:38].ON1C2C=CC=CC=2N=N1.C1(N=C=N)CCCCC1>C(Cl)Cl.C(N(CC)CC)C>[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:19]([NH:29][C@H:30]([C:41]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42])[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[NH:40])[NH:36][N+:37]([O-:39])=[O:38])=[O:21])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[Cl:14])=[O:9]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 7269331Boc-Lys(2-Cl-Z)-OHHCID 12048208N-CyclohexylcarbodiimideHCID 178512187HCID 178512187, compound

Product 1

HCID 178454176HCID 178454176, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Boc-Lys(Cl-Z)-OH (4.15 g), H-Arg(NO2)OBzl.2TsOH (6.54 g) and 1-hydroxybenzotriazole (1.35 g) were dissolved in methylene chloride (70 ml) and then triethylamine (2.02 g) was added, followed by addition of cyclohexylcarbodiimide (2.06 g) under ice-cooling. The temperature was raised to room temperature. The mixture was stirred for 4 hours and then filtered. The filtrate was concentrated and extracted with ethyl acetate. The extract was washed with water, dilute sodium hydrogen carbonate, water and sodium chloride in that order, dried over magnesium sulfate, and concentrated to give Boc-Lys(Cl-Z)-Arg(NO2)-OBzl (7.29 g) as an amorphous solid.

Workup

  1. temperaturecooling
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water, dilute sodium hydrogen carbonate, water and sodium chloride in that order
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06778d99d0ce42dbb4c73bdfee92cb92
Source dataset
uspto-grants-1985_02
Patent number
US04497801

Reaction notes

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