Triethylamine → Boc-Dap-OH

HRID 2261524Notes

Reaction equation

HRID 2261524 reaction equation
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[C:8]2[CH:7]=[C:6]([S:17](Cl)(=[O:19])=[O:18])[CH:5]=[CH:4][C:3]1=2.[NH:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][NH2:24].C(N(CC)CC)C>ClCCl>[NH:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][NH2:24].[C:31]([O:30][C:28]([NH:21][CH:22]([CH2:23][NH:24][S:17]([C:6]1[CH:5]=[CH:4][C:3]2[N:2]([CH3:1])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[C:8]=2[CH:7]=1)(=[O:19])=[O:18])[C:25]([OH:27])=[O:26])=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2755946Boc-Dap-OHHCID 578791559,10-Dihydro-10-methyl-9-oxo-2-acridinesulfonyl chloride

Product 2

HCID 2755946Boc-Dap-OHHCID 57879158HCID 57879158, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

110 mg of the material (2) shown in Table 2 was dissolved in 12 ml of dichloromethane (DCM) (Wako Pure Chemical). 80 mg of Boc-Dap-OH (Bachem) was added to the solution, and then 6 ml of triethylamine (TEA) (Wako Pure Chemical) was added little by little, followed by stirring at room temperature overnight. After the reaction was over, the reaction solution was subjected to evaporation by an evaporator to remove the solvent, supplied with 5% NaHCO3(aq), and further supplied with 0.3 N HCl until the solution got acidic to form a precipitate, which was then filtered by suction and dried in a desiccator. Boc-Dap-OH and the compound (3) thus obtained, 2-tert-butoxycarbonylamino-3-(10-methyl-9-oxo-9,10-dihydro-acridine-2-sulfonylamino)-propionic acid were analyzed to get their respective 1H-NMR data. The results are shown in FIG. 6 and FIG. 7. The product was further purified by silica gel column chromatography to give a substance, which was then analyzed to give the 1H-NMR data. The result was shown in FIG. 8.

Workup

  1. customwas subjected to evaporation by an evaporator
  2. customto remove the solvent
  3. customto form a precipitate, which
  4. filtrationwas then filtered by suction
  5. customdried in a desiccator

Sources & evidence

ORD record
ord-115fe0dc189e47e8b7fc9ce2f2d378f1
Source dataset
uspto-grants-2010_12
Patent number
US07847098B2

Reaction notes

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