Triethylamine → (R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide

HRID 1823018노트

반응식

HRID 1823018 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@H:15]([C:19](O)=[O:20])[CH2:14]2)=[CH:9][CH:8]=1.[CH2:25]([N:27](CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN>CN(C)C=O.C(Cl)Cl>[CH3:25][NH:27][C:19]([C@@H:15]1[CH2:16][C:17](=[O:18])[N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]3[CH:22]=[CH:23][CH:24]=[C:2]([F:1])[CH:3]=3)=[CH:8][CH:9]=2)[CH2:14]1)=[O:20]

참가 물질

7

반응물 4

HCID 8471Triethylamine2회HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 6364545Methylamine hydrochlorideHCID 67409315(S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid

생성물 1

HCID 10020247(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A solution of 0.339 g (1.03 mmol) of (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid in 21 ml of N,N-dimethylformamide, cooled to 0° C., is treated consecutively with 0.15 ml (1.13 mmol) of triethylamine, 0.390 g (1.03 mmol) of HBTU, 0.085 g (1.24 mmol) of methylamine hydrochloride, and 0.15 ml (1.13 mmol) of triethylamine. The reaction is stopped after 30 min and the orange colored solution is evaporated under reduced pressure. The residue obtained is triturated in ethyl acetate, the white solid product is filtered, thereafter dissolved in dichloromethane and the solution washed three times with water. The organic phase is dried over sodium sulfate, then evaporated under reduced pressure to yield 231 mg (66% of theory) of a white solid. MS: m/e=343 (M+H)+; [α]589=−25.48° (c=0.954, CH2Cl2).

후처리

  1. customthe orange colored solution is evaporated under reduced pressure
  2. customThe residue obtained
  3. customis triturated in ethyl acetate
  4. filtrationthe white solid product is filtered
  5. dissolutiondissolved in dichloromethane
  6. washthe solution washed three times with water
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated under reduced pressure
  9. customto yield 231 mg (66% of theory) of a white solid

출처 및 근거

ORD 기록
ord-33cba6c66bf8469ebdfda023b09d112d
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037935B2

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