Methyl chloroformate → HCID 10354936, compound

HRID 2393110Notes

Reaction equation

HRID 2393110 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl[C:18]([O:20][CH3:21])=[O:19]>O>[CH3:21][O:20][C:18]([NH:11][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[C:12]([OH:14])=[O:13])=[O:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide4×HCID 2211922-amino-2-(4-nitrophenyl)acetic acid

Product 1

HCID 10354936HCID 10354936, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of (±)-2-(4-nitrophenyl)glycine (20) (Heyns et al., Justus Lieberg's Annalen der Chimie 611:55-56 (1958)) (3.2400 g, 16.5 mmol) and NaOH (0.6611 g, 16.5 mmol) in water (150 mL) were added methyl chloroformate (1.404 mL, 18.2 mmol), 2N NaOH (9.1 mL), and water (6 mL) at 0° C. After adjusting pH to 9 with 2N NaOH (1 mL) and stirring at 25° C. for 17 h, the mixture was basified to pH 10 with 2N NaOH and washed with diethyl ether before it was acidified with 5N HCl in the presence of EtOAc. The organic fractions (1 L) were dried (MgSO4) and evaporated to yield 19 (3.62 g, 86%): mp 152° C.; 1H NMR (DMSO-d6) δ 3.53 (s, 3H, OCH3), 5.35 (d, J=8.7 Hz, 1H, CH), 7.66 (d, J=8.4 Hz, 2H, aromatic), 8.20 (d, J=8.4 Hz, 3H, aromatic and NH). MS (FAB) m/z 255.0.

Workup

  1. washwashed with diethyl ether before it
  2. dry with materialThe organic fractions (1 L) were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-66b124fcc0254832bfa697652bcdc2e2
Source dataset
uspto-grants-1998_09
Patent number
US05804595

Reaction notes

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