1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[4-(3-Adamantan-1-yl-ureido)-butyryloxymethyl]-benzoic acid ethyl ester

HRID 444680

Reaction equation

HRID 444680 reaction equation
[C:1]12([NH:11][C:12](=[O:20])[NH:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:21]([O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31]O)=[CH:27][CH:26]=1)[CH3:22].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:21]([O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][NH:13][C:12]([NH:11][C:1]23[CH2:8][CH:7]4[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]4)[CH2:10]2)[CH2:2]3)=[O:20])=[CH:27][CH:26]=1)[CH3:22]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 114259954-(3-Adamantan-1-yl-ureido)butyric acidHCID 12480307Ethyl 4-(hydroxymethyl)benzoate

Product 1

HCID 112821754-[4-(3-Adamantan-1-yl-ureido)-butyryloxymethyl]-benzoic acid ethyl esterYield 76.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-adamantan-1-yl-ureido)butyric acid 822 (1.23 g, 0.83 mmol), DMAP (0.05 g, 0.42 mmol), and the above alcohol (0.15 g, 0.83 mmol) in methylene chloride (30 mL) was added EDCI (0.16 g, 0.83 mmol) at room temperature. After stirring for 12 h, the reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL), and the organic layer was dried over Na2SO4 and concentrated. Then the residue was purified by column chromatography on silica gel eluting hexane and ethyl acetate (5:1) to provide 849 (0.28 g, 75%) as a white solid: 1H NMR (CDCl3) 1.40 (3H, t, J=6.9 Hz), 1.66-1.68 (6H, m), 1.84 (2H, quint, J=6.9 Hz), 1.94-1.96 (6H, m), 2.05-2.07 (3H, m), 2.44 (2H, t, J=6.9 Hz), 3.17 (2H, q, J=6.9 Hz), 4.02 (1H, s), 4.17 (1H, s), 4.38 (2H, q, J=6.9 Hz), 5.17 (2H, s), 7.40 (2H, d, J=7.8 Hz), 8.00 (2H, d, J=7.8 Hz); LC-MS (ESI) m/z calcd for C25H34N2O5 [M+H]+ 443.25. found [M+H]+ 443.25; mp 96-99 C. Anal. (C25H34N2O5) C, H, N.

Workup

  1. washthe reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL)
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThen the residue was purified by column chromatography on silica gel
  5. washeluting hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-4a38f22b55604cb89a249b45021cfada
Source dataset
uspto-grants-2013_07
Patent number
US08476043B2

Linked notes

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