Sodium Hydroxide → (1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)cyclopent-2-enecarboxylic acid

HRID 1747118노트

반응식

HRID 1747118 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])([C:14]([OH:16])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 86708127(1S,4S)-methyl 4-(tert-butoxycarbonylamino)-1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopent-2-enecarboxylate

생성물 1

HCID 86708128(1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)cyclopent-2-enecarboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of the product of Step A (7.89 g, 19.74 mmol, 1 eq) in methanol (100 mL) at rt was added 1 N NaOH (59.2 mL, 59.2 mmol, 3.0 eq). After stirring overnight, the methanol was removed, 1 N HCl was added until the solution was acidic, the solution extracted with DCM, the organics combined, dried over MgSO4, and concentrated to afford the title compound of Step B. 1H NMR (CHLOROFORM-d) δ: 5.85 (br. s., 2H), 4.97 (br. s., 1H), 4.80 (br. s., 1H), 3.71 (br. s., 2H), 1.99-2.41 (m, 3H), 1.92 (br. s., 1H), 1.44 (br. s., 9H), 0.88 (s, 9H), 0.06 (br. s., 6H). ESI-MS (m/z): Calculated for C19H35NO5Si: 408.2 (M+23). found: 408.3.

후처리

  1. customthe methanol was removed
  2. addition1 N HCl was added until the solution
  3. extractionthe solution extracted with DCM
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dd229b987ae84d808979daa0558661f5
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150532B2

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