Hydrochloric Acid → N-{[6-Nitro-2,3-dihydro-1(1H)-isoindolone-2-yl]acetyl}-3(R)-methyl-beta-alanine benzyl ester

HRID 862437Notes

Reaction equation

HRID 862437 reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([O:11]C)=O)=[CH:7][C:6]([N+:13]([O-:15])=[O:14])=[CH:5][CH:4]=1.[CH2:16]([O:23][C:24](=[O:40])[CH2:25][C@@H:26]([CH3:39])[NH:27][C:28](=[O:38])[CH2:29][NH:30]C(OC(C)(C)C)=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)C.Cl>C(#N)C>[CH2:16]([O:23][C:24](=[O:40])[CH2:25][C@@H:26]([CH3:39])[NH:27][C:28](=[O:38])[CH2:29][N:30]1[CH2:2][C:3]2[C:8](=[CH:7][C:6]([N+:13]([O-:15])=[O:14])=[CH:5][CH:4]=2)[C:9]1=[O:11])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1146TrimethylamineHCID 14552709Methyl 2-(bromomethyl)-5-nitrobenzoateHCID 86751222N-t-Butoxycarbonylglycyl-3(R)-methyl-beta-alanine benzyl ester

Product 1

HCID 86752090N-{[6-Nitro-2,3-dihydro-1(1H)-isoindolone-2-yl]acetyl}-3(R)-methyl-beta-alanine benzyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 6-bromomethyl-3-nitrobenzoate (430 mg, 1.64 mmol), N-glycyl-3(R)-methyl-β-alanine benzyl ester hydrochloride 2-4 (611 mg, 2.13 mmol) and trimethylamine (0.68 mL, 4.92 mmol) were stirred fin acetonitrile (10 mL) for 16 hours. The solution was poured into 1N HCl and extracted with EtOAc (3×), washed with brine, dried (MgSO4) and evaporated. Purification by column chromatography eluting with EtOAc afforded 2-6 as a solid. Rf (silica; EtOAc)=0.45. ##STR60## N-{[6-Amino-2,3-dihydro-1(1H)-isoindolone-2-yl]acetyl}-3(R)-methyl-β-alanine (2-7)

Workup

  1. extractionextracted with EtOAc (3×)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by column chromatography
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-4614d0ef461141208b896c13510e447f
Source dataset
uspto-grants-1998_02
Patent number
US05719144

Reaction notes

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