Diisopropylethylamine → {2-[(4'-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid diethylester

HRID 1642062Notes

Reaction equation

HRID 1642062 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH2:17]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38](O)=[O:39])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CCN(C(C)C)C(C)C.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.C(Cl)CCl>[CH2:6]([O:5][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:38]([C:35]1[CH:34]=[CH:33][C:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:27][CH:28]=2)=[CH:37][CH:36]=1)=[O:39])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acidHCID 13649220Diethyl [(2-aminophenyl)methyl]phosphonate

Product 1

HCID 86638333{2-[(4'-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid diethylester

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 g of (2-amino-benzyl)-phosphonic acid diethyl ester, 2 g of 4′-octyloxy-biphenyl-4-carboxylic acid, 1.4 ml of EDC, 0.9 ml of DIEA and 100 mg of HOAt are dissolved in 30 ml of DMF and the mixture obtained is stirred at rt for 2 days. The mixture obtained is diluted with EtOAc and the solution obtained is washed with aqueous diluted HCl and aqueous NaHCO3 solution. The organic layer obtained is dried and solvent is evaporated. {2-[(4′-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid diethylester is obtained in crystalline form and is recrystallized from iso-propanol/water.

Workup

  1. customthe mixture obtained
  2. customThe mixture obtained
  3. customthe solution obtained
  4. washis washed with aqueous diluted HCl and aqueous NaHCO3 solution
  5. customThe organic layer obtained
  6. customis dried
  7. customsolvent is evaporated

Sources & evidence

ORD record
ord-310c25592dd84c46b45f0c5c1a7438c8
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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