Acetic Acid → HCID 22990564, 화합물

HRID 1169286노트

반응식

HRID 1169286 반응식
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH2:21]([NH:28][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[C:9]([Cl:10])[C:2]=1[Cl:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22990571HCID 22990571, 화합물

생성물 1

HCID 22990564HCID 22990564, 화합물

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of Example 5B (65 mg, 0.22 mmol) and benzylamine (0.024 mL, 0.22 mmol) in 1,2-dichloroethane (3 mL) at room temperature was treated with acetic acid (0.05 mL, 0.84 mmol), stirred for 2 hours, treated with sodium triacetoxyborohydride (64 mg, 0.31 mmol), stirred for 16 hours, and treated with saturated NaHCO3. The organic layer was dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate to ethyl acetate to provide the desired product. MS (ESI(+)) m/z 393 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ7.92 (d, 2H), 7.56-7.46 (m, 3H), 7.45-7.26 (m, 9H), 4.05 (s, 2H), 3.93 (s, 2H).

후처리

  1. stirringstirred for 16 hours
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate to ethyl acetate

출처 및 근거

ORD 기록
ord-cf153a711d1644e8ae187c6cd6579bfe
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627767B2

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