Glutamic acid diethyl ester hydrochloride → 2-[(5-Bromo-3-methyl-thiophene-2-carbonyl)-amino]-glutamic acid diethyl ester

HRID 1532973

反応式

HRID 1532973 の反応式
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[C:4]([CH3:10])[CH:3]=1.O.O[N:13]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.[CH2:32]([O:34][C:35](=[O:45])[C@H:36]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[NH2:37])[CH3:33].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH2:32]([O:34][C:35](=[O:45])[C@:36]([NH:13][C:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10])=[O:9])([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[NH2:37])[CH3:33]

参加物

8

反応物 5

HCID 73960Glutamic acid diethyl ester hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 181766635-Bromo-3-methylthiophene-2-carboxylic acid

生成物 1

HCID 701466202-[(5-Bromo-3-methyl-thiophene-2-carbonyl)-amino]-glutamic acid diethyl ester収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 10.86 g (49.1 mmol) of 5-Bromo-3-methyl-thiophene-2-carboxylic acid (prepared according to D. Spinelli, JCS Perkin Trans. II, 1972, 1866), 6.97 g (51.6 mmol) of 1-Hydroxybenzotriazole hydrate, 9.0 mL (51.7 mmol) of diisopropylethylamine and 12.36 g (51.6 mmol) of L-glutamic acid diethyl ester hydrochloride in 70 mL of DMF was added 9.89 g (51.6 mmol) of 1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride. The reaction mixture was stirred under Argon for 18 hours, poured into H2O and extracted with ethyl acetate. The organic layer was washed sequentially with 0.5N HCl, saturated NaHCO3 soln and saturated NaCl soln, dried over MgSO4, then concentrated under reduced pressure. This residue was purified by flash chromatography on silica gel eluting methylene chloride-ethyl acetate (20:1). In this manner, there was obtained 19.70 g (99%) of the desired product as a colorless oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed sequentially with 0.5N HCl, saturated NaHCO3 soln
  3. dry with materialsaturated NaCl soln, dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThis residue was purified by flash chromatography on silica gel
  6. washeluting methylene chloride-ethyl acetate (20:1)

出典と根拠

ORDレコード
ord-b5ea892ce3604b62975f8b1cceaf0d0b
出典データセット
uspto-grants-2001_03
特許番号
US06207670B1

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