Hydrazine hydrate (1:1) → HCID 69530304, compound

HRID 1814433Notes

Reaction equation

HRID 1814433 reaction equation
[C:1]1(=[O:31])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([CH:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])C(=O)C2=CC=CC=C12.O.NN.[CH2:35]([O:37][C:38]([C:40]1[CH:45]=[CH:44][C:43]([N:46]=C=O)=[CH:42][CH:41]=1)=[O:39])[CH3:36]>CCO>[CH2:35]([O:37][C:38]([C:40]1[CH:41]=[CH:42][C:43]([NH:46][C:1](=[O:31])[NH:5][CH2:6][CH2:7][CH2:8][N:9]([CH:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:44][CH:45]=1)=[O:39])[CH3:36]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 589805Ethyl 4-isocyanatobenzoateHCID 69529871HCID 69529871, compound

Product 1

HCID 69530304HCID 69530304, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[[(3-phthalimido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (137 mg, 0.32 mmol) in EtOH (5 ml) was added hydrazine monohydrate (63 μl, 1.3 mmol), and the mixture was stirred at RT for 4 h. The reaction mixture was concentrated under vacuum, and then water was added. The mixture was extracted with chloroform, washed with water and brine, dried over sodium sulfate, and filtered. To the filtrate was added 4-(ethoxycarbonyl)phenyl isocyanate (62 mg, 0.32 mmol), and the mixture was stirred at RT for 30 min. The reaction mixture was concentrated under vacuum to dryness, and the residue was adsorbed on a plate of silica gel and then developed with 17% methanol/chloroform to afford 4-[[3-[4-(ethoxycarbonyl)phenylureido]propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (25 mg, 16%): MS(ES+) m/e 482 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 9.86 (s, 1H), 8.80 (br, 1H), 7.91 (m, 3H), 7.61 (m, 3H), 7.21 (m, 1H), 7.12 (m, 2H), 4.70 (t, J=7.6 Hz, 1H), 4.33 (q, J=7.1 Hz, 2H), 3.32 (m, 2H), 3.23 (m, 1H), 3.03-2.84 (m, 3H), 2.74 (m, 2H), 2.55 (m, 1H), 2.21 (m, 2H), 2.02-1.78 (m, 5H), 1.70 (m, 2H), 1.37 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionwater was added
  3. extractionThe mixture was extracted with chloroform
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. stirringthe mixture was stirred at RT for 30 min
  8. concentrationThe reaction mixture was concentrated under vacuum to dryness

Sources & evidence

ORD record
ord-0c3db6a7157e46d0be7fcfad29884a35
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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