Lithium Hydroxide → HCID 3836387, compound

HRID 1616797Notes

Reaction equation

HRID 1616797 reaction equation
[CH2:1]([NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14]CC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C(O)C>[CH2:1]([NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10568143HCID 10568143, compound

Product 1

HCID 3836387HCID 3836387, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(3-benzylureido)-3-phenylpropanoate 13 (2.66 mmol, 0.83 g) and 2 N lithium hydroxide (5.32 mmol, 0.22 g) in ethanol (20 mL) was kept in stirring overnight at room temperature. The reaction was quenched by addition of 2 N HCl until pH=2, afterwards the precipitate was filtered, washed with water (3×30 mL) and dried to obtain the pure 2-(3-benzylureido)-3-phenylpropanoic acid as a pale white solid; 95% yield, m.p. 115-117° C.; recryst. solvent: cyclohexane/benzene; 1H NMR (CDCl3, 400 MHz, δ; ppm) δ 2.85-2.87 (dd, 1H, PhCHHCHCOO), 2.89-2.91 (dd, 1H, PhCHHCOO), 4.38-4.40 (m, 1H, PhCHHCHCOO), 6.14-6.17 (d, 1H, PhCHHNHCONH), 6.54-6.57 (m, 1H, PhCHHNHCONH), 7.18-7.30 (m, 10H, aromatic protons), 12.65 (bs, 1H, COOH); 13C NMR (CDCl3, 400 MHz, δ; ppm) δ 36.0, 44.4, 56.8, 125.9, 126.7, 126.9 (2C), 127.7 (2C), 128.5 (2C), 128.6 (2C), 136.6, 137.9, 157.6, 174.7; MS (ESI) m/z: 298.32 [M]+.

Workup

  1. customThe reaction was quenched by addition of 2 N HCl until pH=2
  2. filtrationafterwards the precipitate was filtered
  3. washwashed with water (3×30 mL)
  4. customdried

Sources & evidence

ORD record
ord-41f6939d0b5b4e0ba10872258cfdd169
Source dataset
uspto-grants-2014_07
Patent number
US08765820B2

Reaction notes

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