Picolinic acid → HCID 70247755, 화합물

HRID 636286

반응식

HRID 636286 반응식
[C:1]1([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[CH:11]1[CH:12]=[CH:13][C:14]2N(O)N=[N:17][C:15]=2[CH:16]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27](O)=[O:28].CN([P+]([O:40]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[Na+].[Cl-]>CN(C=O)C.O.CCOC(C)=O>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([NH:8][CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:9][NH:10][C:16](=[O:40])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][N:17]=2)[CH:2]=1)=[O:28]

참가 물질

9

반응물 5

HCID 1018Picolinic acidHCID 5234Sodium ChlorideHCID 151331,3-BenzenedimethanamineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

생성물 1

HCID 70247755HCID 70247755, 화합물수율 103.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 1,3-xylylenediamine (132 uL, 1.00 mmol) in DMF (10 mL) was sequentially added IPr2NEt (1.75 mL, 10.0 mmol), HOBt (405 mg, 3.00 mmol), picolinic acid (370 mg, 3.00 mmol) and BOP reagent (1.33 g, 3.00 mmol). After 18 h at room temperature, the reaction mixture was added to a rapidly-stirred mixture of EtOAc (50 mL), H2O (50 mL), and sat'd NaCl (50 mL). After stirring for ca 1 h, the phases were separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to a brown oil. Purification by flash chromatography (silica gel, EtOAc) afforded 359 mg of the desired product as a white solid. MS (ES+) m/z 347.2 [M+H]+.

후처리

  1. customthe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a brown oil
  6. customPurification by flash chromatography (silica gel, EtOAc)

출처 및 근거

ORD 기록
ord-80ac522f774a415da7cfb328b872673e
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06191146B1

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