Hexamethylphosphoramide → HCID 10961504、化合物

HRID 336212

反応式

HRID 336212 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 10961504HCID 10961504、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-a314b8452555435e9290bcb694219f81
出典データセット
uspto-grants-2014_11
特許番号
US08889670B2

関連ノート

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