1-Hydroxybenzotriazole → HCID 67103783, compound

HRID 2080893Notes

Reaction equation

HRID 2080893 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([NH:16][C:17]([O:19][CH2:20][CH:21]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:34]1C=CC2N(O)N=NC=2[CH:39]=1.CCN=C=NCCCN(C)C.Cl>C(O)C>[CH2:34]([O:14][C:13](=[O:15])[C@H:12]([NH:16][C:17]([O:19][CH2:20][CH:21]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH3:39]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13996154N~5~-(tert-Butoxycarbonyl)-N~2~-{[(9H-fluoren-9-yl)methoxy]carbonyl}-D-ornithine

Product 1

HCID 67103783HCID 67103783, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (60 ml), 5-t-butoxycarbonylamino-(2R)-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid (1.9914 g) was dissolved. The solution was added with HOBt (770.2 mg) and WSCI hydrochloride (1.0927 g) and the whole was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with 1 mol/l hydrochloric acid, a 1 mol/l sodium hydroxide aqueous solution, and a saturated saline solution, followed by drying with magnesium sulfate. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.9846 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l hydrochloric acid
  5. dry with materialby drying with magnesium sulfate
  6. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-82ebe6b7ed5d4735a6e4ab63ac2f88d8
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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