Acetic Acid → HCID 77174872, 화합물

HRID 1696295노트

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HRID 1696295 반응식
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](O)(=O)[CH3:8].S([O-])([O-])(=O)=O.[Mg+2].[O:17]1[CH:22]([C:23]([OH:25])=[O:24])[CH2:21][NH:20][C:19]2[CH:26]=[CH:27][CH:28]=[CH:29][C:18]1=2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]1([N:20]2[CH2:21][CH:22]([C:23]([O:25][CH2:7][CH3:8])=[O:24])[O:17][C:18]3[CH:29]=[CH:28][CH:27]=[CH:26][C:19]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 38269523,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acidHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 77174872HCID 77174872, 화합물

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매2회

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온도
25 °C

실험 절차

Cyclopentanone (83 L, 0.94 mmol), acetic acid (54 L, 0.94 mmol), and magnesium sulfate (113 mg, 0.94 mmol) were added to a solution of (±)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid (Example 3a, 65 mg, 0.31 mmol) in dichloroethane (1.25 mL). Sodium triacetoxyborohydride (100 mg, 0.47 mmol) was added, followed by dichloroethane (1.25 mL), and the suspension was stirred at 25° C. for 48 h. The reaction mixture was quenched with half-saturated sodium bicarbonate, and the product was extracted using 67% EtOAc/hexane (3×25 mL). The combined organic fractions were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (10% EtOAc/hexane) afforded the title compound as an oil. MS m/z: 276 (M+1).

후처리

  1. customThe reaction mixture was quenched with half-saturated sodium bicarbonate
  2. extractionthe product was extracted
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification of the product by flash column chromatography (10% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-3326df04580f4a8882341067f04b2478
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163766B2

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