Triethylamine → 1-Benzhydryl-N-methylazetidine-3-carboxamide

HRID 492916노트

반응식

HRID 492916 반응식
[CH:1]([N:14]1[CH2:17][CH:16]([C:18]([OH:20])=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([N:23](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.CN>CN(C)C=O>[CH3:21][NH:23][C:18]([CH:16]1[CH2:17][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15]1)=[O:20]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acidHCID 6364545Methylamine hydrochloride

생성물 1

HCID 137728491-Benzhydryl-N-methylazetidine-3-carboxamide수율 74.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-benzhydrylazetidin-3-carboxylic acid (654 mg) in N,N-dimethylformamide (4.0 ml) were added triethylamine (1.0 ml), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.63 g) and methylamine hydrochloride (248 mg), followed by stirring at room temperature for 61.5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated to give a residue, which was purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to provide the titled compound (509 mg, 74.1%) as yellow crystals.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography (eluent; ethyl acetate)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated

출처 및 근거

ORD 기록
ord-4d1f8cbffce44eb39e7d2ebbeadc5db5
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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