HCID 59355026, compound → 3-amino-2-benzylpropanoic acid

HRID 2047347Notes

Reaction equation

HRID 2047347 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(CC(OCC)=O)[C:14]([O:16]CC)=[O:15]>Cl.CC(O)=O>[NH2:3][CH2:12][CH:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:14]([OH:16])=[O:15]

Participants

4

Reactant 1

HCID 59355026HCID 59355026, compound

Product 1

HCID 2779393-amino-2-benzylpropanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A solution of diethyl 2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-(phenylmethyl)butanedioate (13 g, 31.8 mmole) in conc. HCl (125 mL) and HOAc (30 mL) was sealed in a 1 L screwcap reaction vessel and the contents heated to 120° C. for 48 h. The reaction solution was concentrated under vacuum and the resulting solids washed with Et2O affording the title compound (quant.) as a white solid: LCMS (ES) m/z 181(M+H)+.

Workup

  1. concentrationThe reaction solution was concentrated under vacuum
  2. washthe resulting solids washed with Et2O affording the title compound (quant.) as a white solid

Sources & evidence

ORD record
ord-3727fd93e2974e2cb6a416656649ad82
Source dataset
uspto-grants-2013_11
Patent number
US08592475B2

Reaction notes

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