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Triethylamine → 2-[Cyclopropyl-(3-morpholin-4-yl-5-trifluoromethyl-benzoyl)-amino]-3-oxo-butyric acid ethyl ester

HRID 545358
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HRID 545358 반응식
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH:6]([NH:10][CH:11]1[CH2:13][CH2:12]1)[C:7](=[O:9])[CH3:8])[CH3:3].[N:15]1([C:21]2[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=2)[C:24](O)=[O:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[CH2:2]([O:4][C:5](=[O:14])[CH:6]([N:10]([CH:11]1[CH2:12][CH2:13]1)[C:24](=[O:25])[C:23]1[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=[C:21]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:22]=1)[C:7](=[O:9])[CH3:8])[CH3:3]
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 220579413-Morpholin-4-yl-5-trifluoromethyl-benzoic acidHCID 671330592-Cyclopropylamino-3-oxo-butyric acid ethyl ester hydrochloride salt

생성물 1

HCID 67133209
2-[Cyclopropyl-(3-morpholin-4-yl-5-trifluoromethyl-benzoyl)-amino]-3-oxo-butyric acid ethyl ester
수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 0.4 g (2 mmol) of 2-cyclopropylamino-3-oxo-butyric acid ethyl ester hydrochloride salt, 0.6 g (2 mmol) of 3-morpholin-4-yl-5-trifluoromethyl-benzoic acid, 0.4 g (2 mmol) of EDCI and 0.3 g (2 mmol) of HOBT was added 2 ml of DMF and 0.6 ml (4 mmol) of triethylamine. The mixture was stirred for 3 h after which time the solvent was removed by evaporation; the residue was then re-dissolved in EtOAc, washed with 10% citric acid solution, saturated sodium hydrogen carbonate solution, dried with sodium sulfate and re-concentrated to afford 0.8 g (93%) of crude 2-[cyclopropyl-(3-morpholin-4-yl-5-trifluoromethyl-benzoyl)-amino]-3-oxo-butyric acid ethyl ester. This material was re-dissolved in 5 ml of EtOH and 1 g (8 mmol) of ammonium trifluoroacetate was added. The solvent was evaporated and the residue heated to 130° C. for 16 h. The cooled residue was partitioned between saturated sodium hydrogen carbonate solution and CH2Cl2. The organic phase was dried with sodium sulfate and concentrated. Purification by flash column chromatography [n-heptane/EtOAc 6:4] afforded 0.4 g (55%) of the title compound as colorless solid. MS: 424.2 (MH+).

후처리

  1. customwas removed by evaporation
  2. dissolutionthe residue was then re-dissolved in EtOAc
  3. washwashed with 10% citric acid solution, saturated sodium hydrogen carbonate solution
  4. dry with materialdried with sodium sulfate
  5. concentrationre-concentrated

출처 및 근거

ORD 기록
ord-820ba63abaf149b9bdb2639d751d93a9
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935707B2

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