Phenyl isocyanate → HCID 13572158, compound

HRID 1373085Notes

Reaction equation

HRID 1373085 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(N(CC)CC)C.[C:15]1([N:21]=[C:22]=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:22]([NH:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:23]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 13572158HCID 13572158, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of glycine methyl ester hydrochloride (4.52 g, 36 mmol) in methylene chloride (200 mL) was added triethylamine (5.0 mL, 36 mmol) at room temperature and stirred for 15 minutes. To the reaction mixture was added dropwise phenyl isocyanate (3.57 g, 30 mmol). The reaction mixture was stirred at room temperature for 2 hours and washed with 1N HCl (2×80 mL) and brine (80 mL). The organic layer was dried (Na2SO4) and concentrated to give the ester compound (6.2 g, ˜100%). 1H NMR (400 MHz, DMSO-d6) δ: 8.80 (s, 1H), 7.39 (d, 2H), 7.22 (t, 2H), 6.89 (m, 1H), 6.45 (t, 1H), 3.88 (d, 2H), 3.66 (s, 3H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. washwashed with 1N HCl (2×80 mL) and brine (80 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b6b5cbd9c6d4d1fa9e60109e5b7602a
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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