Triethylamine → HCID 11351277, compound

HRID 1271001Notes

Reaction equation

HRID 1271001 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])[N:9]([C@H:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[CH3:10])=[CH:3][CH:2]=1.[CH2:29]([N:31]([CH2:34]C)[CH2:32]C)[CH3:30].C[NH:37][C@@H](CC1C=CC=CC=1)C(O)=O.C1(C2C=CC=CC=2)C=CC(N=C=O)=CC=1>C1COCC1.CC(C)=O.O>[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])[N:9]([C@H:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([NH:37][CH2:30][CH2:29][N:31]([CH3:34])[CH3:32])=[O:14])[CH3:10])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 36123194-Biphenylyl isocyanateHCID 6951135N-Methylphenylalanine2×HCID 69433759HCID 69433759, compound

Product 1

HCID 11351277HCID 11351277, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

(R)-2-(3-Biphenyl-4-yl-1-methyl-ureido)-3-phenyl-propionic acid. Triethylamine (0.17 g, 1.68 mmol) was added to a suspension of (S)-2-methylamino-3-phenyl-propionic acid (0.2 g, 1.12 mmol) in 1:1 acetone/H2O (80 mL). Once the (S)-2-methylamino-3-phenyl-propionic acid dissolved, 4-biphenylyl isocyanate (0.228 g, 1.17 mmol) was added as a solution in THF (1.5 mL) at 0° C. As the mixture was warmed to rt, solids crashed out of solution. The mixture was stirred for 7 h at rt, and then the solvents were removed. After acidifying with 1 N HCl (10 mL) to bring the pH to 2, the reaction mixture was filtered, and the aqueous filtrate was extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine and dried (MgSO4), and the solvent was removed. Column chromatography using [5–20% (1% NH4OH/MeOH)/CH2Cl2] afforded 0.1 g (24%) of the desired product. MS (electrospray): mass calculated for C23H22N2O3, 374.16; m/z found, 375.1 [M+H]+, 397.1 [M+Na]+. 1H NMR (400 MHz, CD3OD): 7.63–7.59 (m, 4H), 7.45–7.41 (m, 2H), 7.36–7.29 (m, 4H), 7.23–7.21 (m, 2H), 7.04–7.01 (m, 2H), 4.48 (t, J=4.1 Hz, 1H), 3.37–3.33 (m, 1H), 3.25 (dd, J=14.4, 3.8 Hz, 1H), 3.10 (s, 3H).

Workup

  1. customthe solvents were removed
  2. filtrationthe reaction mixture was filtered
  3. extractionthe aqueous filtrate was extracted with EtOAc (3×40 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-bde52ad606cc41eaaef20a2ca60435e6
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

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