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

HRID 862437ノート

反応式

HRID 862437 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-4614d0ef461141208b896c13510e447f
出典データセット
uspto-grants-1998_02
特許番号
US05719144

反応ノート

読み込み中…