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

HRID 2085724노트

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HRID 2085724 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-efad821a118045f68de0b2518d06cad2
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720338B2

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