tert-Butyl Formate → HCID 68596726, 화합물

HRID 270614

반응식

HRID 270614 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([C@H:18]2[CH2:22][CH2:21][O:20][CH2:19]2)([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].C(OC(C)(C)C)=O>O1CCCC1.CO.O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([C@H:18]2[CH2:22][CH2:21][O:20][CH2:19]2)([C:14]([OH:16])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 3

HCID 61207tert-Butyl FormateHCID 168937Lithium hydroxide, monohydrateHCID 68930507HCID 68930507, 화합물

생성물 1

HCID 68596726HCID 68596726, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl (1R,4S)-4-[(tert-butoxycarbonyl)amino]-1-[(3R)-tetrahydrofuran-3-yl]cyclopent-2-ene-1-carboxylate (1.60 g, 5.14 mmol) in tetrahydrofuran (27.8 mL), methanol (27.8 mL) and water (6.0 mL) was added lithium hydroxide monohydrate (0.346 g, 8.25 mmol). The pink mixture was heated to reflux for 18 h. The organic solvents were removed in vacuo and the aqueous layer was extracted once with ether and then acidified slowly with 6 M HCl until the pH reached 3-4. The resulting suspension was extracted with CH2Cl2 three times. The combined organic layers were dried over MgSO4, filtered and concentrated to give the product as a mixture of two cis/trans isomers (1.59 g) as a light yellow solid. MS calculated for C15H24NO5: (M+H) 298.2; found 198.2 (M+H-Boc).

후처리

  1. temperatureThe pink mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe organic solvents were removed in vacuo
  4. extractionthe aqueous layer was extracted once with ether
  5. extractionThe resulting suspension was extracted with CH2Cl2 three times
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the product
  10. additionas a mixture of two cis/trans isomers (1.59 g) as a light yellow solid

출처 및 근거

ORD 기록
ord-b4af25f1426c499f9d89c7f7dc788b86
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449467B2

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