3-Amino-3-(4-methylphenyl)propanoic acid → HCID 10050407, compound

HRID 1270983Notes

Reaction equation

HRID 1270983 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:22])[NH:9][CH:10]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH2:11][C:12]([OH:14])=O)=[CH:3][CH:2]=1.[NH2:29][CH:30]([C:35]1[CH:40]=[CH:39]C(C)=CC=1)CC(O)=O.[N:42]([C:45]1C=CC(C2C=CC=CC=2)=C[CH:46]=1)=C=O>C(Cl)Cl>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:22])[NH:9][C@@H:10]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH2:11][C:12]([NH:42][CH2:45][CH2:46][N:29]2[CH2:30][CH2:35][CH2:40][CH2:39]2)=[O:14])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 27336803-Amino-3-(4-methylphenyl)propanoic acidHCID 36123194-Biphenylyl isocyanateHCID 184502433-(3-Biphenyl-4-yl-ureido)-3-p-tolyl-propionic acid

Product 1

HCID 10050407HCID 10050407, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(3-Biphenyl-4-yl-ureido)-3-p-tolyl-propionic acid. To a solution of 3-amino-3-(p-tolyl)propionic acid (0.50 g, 2.79 mmol) and TEA (0.26 g, 2.56 mmol) in CH2Cl2 (28 mL) cooled to 0° C., was added 4-isocyanato-biphenyl (0.55 g, 2.79 mmol). The mixture was stirred at 0° C. for 30 min and was then brought to rt and stirred for an additional 3 h. The solvent was removed, water (20 mL) was added to the clear residue, and the mixture was then chilled to 0° C. and acidified using 1 N HCl. The resulting precipitate was collected by filtration, washed with copious amounts of H2O, and dried under vacuum to afford 0.87 g (83%) of the desired product as a white solid. MS (electrospray): mass calculated for C23H22N2O3, 374.16; m/z found, 413.0 [M+Na]+. 1H NMR (400 MHz, DMSO-d6): 8.74 (s, 1H), 7.65–7.29 (m, 9H), 7.25 (d, J=8.1 Hz, 2H), 7.14 (d, J=7.9 Hz, 2H), 6.64 (d, J=8.5 Hz, 1H), 5.11–5.06 (m, 1H), 2.74–2.67 (m, 2H), 2.27 (s, 3H).

Workup

  1. customwas then brought to rt
  2. stirringstirred for an additional 3 h
  3. customThe solvent was removed
  4. additionwater (20 mL) was added to the clear residue
  5. temperaturethe mixture was then chilled to 0° C.
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with copious amounts of H2O
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3cf15431cac14729a55e7d4b8e5abb52
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

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