Dimethylformamide → 3-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-fluorophenyl)-1-oxobutanyl]thiazolidine

HRID 970207노트

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HRID 970207 반응식
[N:1]([C@@H:4]([C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:9])[C:5]([OH:7])=O)=[N+]=[N-].Cl.CN(C)CCCN=C=NCC.[OH:29][C:30]1[C:38]2N=NNC=2C=C[CH:31]=1.[S:39]1[CH2:43][CH2:42][NH:41][CH2:40]1.[CH3:44]CN(C(C)C)C(C)C.CN(C)[CH:55]=[O:56]>C(OCC)(=O)C>[C:30]([O:29][C:55]([NH:1][C@@H:4]([C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:9])[C:5]([N:41]1[CH2:42][CH2:43][S:39][CH2:40]1)=[O:7])=[O:56])([CH3:31])([CH3:38])[CH3:44]

참가 물질

8

반응물 6

HCID 6228DimethylformamideHCID 10444ThiazolidineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86605120(2S,3S)-2-Azido-3-(4-fluorophenyl)butanoic acidHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 694229793-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-fluorophenyl)-1-oxobutanyl]thiazolidine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of the product from Step D (0.19 g, 0.65 mmol) in anhydrous dimethylformamide (DMF, 2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.19 g, 0.99 mmol), hydroxybenzotriazole (HOBT, 0.13 g, 0.96 mmol), thiazolidine (0.26 mL, 3.3 mmol) and N,N′-diisopropylethylamine (0.33 mL, 1.9 mmol). After stirring at room temperature for 12 h, the reaction was diluted with ethyl acetate. The organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution, dried over sodium sulfate, and evaporated in vacuo to yield the crude coupled product, which was used directly in the next step.

후처리

  1. washThe organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customto yield the crude

출처 및 근거

ORD 기록
ord-9e57c806683349efb7c4a76b49115741
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07309714B2

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