Hexamethylphosphoramide → HCID 10961504, 화합물

HRID 336212

반응식

HRID 336212 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11]1([C@@H:17]2[N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][C:20](=[O:30])[O:19][C@@H:18]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]I.CN(P(N(C)C)(N(C)C)=O)C>C1COCC1.CCOC(C)=O>[C:26]([O:25][C:23]([N:22]1[C@@H:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:18]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:19][C:20](=[O:30])[C@@H:21]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][Cl:37])=[O:24])([CH3:29])([CH3:27])[CH3:28]

참가 물질

7

반응물 4

HCID 12679HexamethylphosphoramideHCID 1089141-Chloro-5-iodopentaneHCID 981230tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amide

생성물 1

HCID 10961504HCID 10961504, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

A 1.0M solution of sodium bis(trimethylsilyl)amide in THF (55.0 mL, 55.2 mmol) is added at −78° C. to a solution of (5S,6R)-5,6-diphenyl-4-tert-butoxycarbonyl-morpholin-2-one (13.0 g, 36.8 mmol), 1-chloro-5-iodo-pentane (25.0 g, 108.0 mmol) and HMPA (55.0 mL) in THF (200.0 mL). The reaction mixture is stirred at −78° C. for 2 hours and at room temperature for 1 hour. The reaction mixture is diluted with EtOAc, washed with water and brine. After drying the organic phase over anhydrous Na2SO4, the solvent is removed under reduced pressure to afford the crude product that is purified by silica gel column chromatography to afford the title compound; m/z 358 [M-Boc+H].

후처리

  1. washwashed with water and brine
  2. dry with materialAfter drying the organic phase over anhydrous Na2SO4
  3. customthe solvent is removed under reduced pressure
  4. customto afford the crude product that
  5. customis purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a314b8452555435e9290bcb694219f81
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889670B2

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