Lithium Hydroxide → n-Tert-butoxycarbonyl-1-morpholin-4-yl-1-oxo-3-(phenylthio)propan-2-amine

HRID 2085724ノート

反応式

HRID 2085724 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([O:20]C)=O)[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CCN=C=NCCCN(C)C>CO.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:10][S:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:18]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:20])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

9

反応物 4

HCID 3939Lithium HydroxideHCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

生成物 1

HCID 22730433n-Tert-butoxycarbonyl-1-morpholin-4-yl-1-oxo-3-(phenylthio)propan-2-amine

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of Example 175A (600 mg, 1.92 mmol) and 2M aqueous lithium hydroxide (4 mL) in methanol (10 mL) at room temperature was stirred for 5 hours and concentrated. The concentrate was treated with morpholine (263 mg, 3 mmol), EDCI (555 mg, 2.88 mmol), DMAP (20 mg) and DMF (20 mL), stirred for 16 hours, diluted with ethyl acetate (100 mL), washed sequentially with water (50 mL), and brine (20 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 367 (M+H)+.

後処理

  1. concentrationconcentrated
  2. washwashed sequentially with water (50 mL), and brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-efad821a118045f68de0b2518d06cad2
出典データセット
uspto-grants-2004_04
特許番号
US06720338B2

反応ノート

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