Trimethylphosphine → Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2172995노트

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HRID 2172995 반응식
CP(C)C.[N:5]([C@H:8]1[C@@H:13]2[C@@H:11]([C@H:12]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@:10]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:9]1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=1)=[N+]=[N-].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[NH2:5][C@H:8]1[C@@H:13]2[C@@H:11]([C@H:12]2[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@:10]([NH:28][C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C@@H:9]1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=1

참가 물질

6

반응물 3

HCID 68983TrimethylphosphineHCID 516892Sodium BicarbonateHCID 86695978Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-azido-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

생성물 1

HCID 86695979Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate수율 97%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Add a 1M solution of trimethylphosphine in tetrahydrofuran (19.56 mL, 19.56 mmol) to di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-azido-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (8.00 g, 13.04 mmol) in tetrahydrofuran (43.46 mL) and water (130.39 mL) at room temperature and stir overnight. Saturated aqueous sodium bicarbonate is added to the reaction then extracted with ethyl acetate (3×). The combined organics are washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure giving the title compound (7.42 g, 12.63 mmol, 97%). MS (m/z): 609/611 (M+Na).

후처리

  1. extractionthen extracted with ethyl acetate (3×)
  2. washThe combined organics are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6eb075e923424ea28dd2f086c6780517
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056844B2

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