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

HRID 430531

반응식

HRID 430531 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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-Dimethylamino-propy)-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 0.5 N 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.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed sequentially with 0.5 N 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)

출처 및 근거

ORD 기록
ord-5ca7a4bcc70146b8bef62b14b5aa1b61
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323210B2

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