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N-Methylbenzeneethanamine → [2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

HRID 491914
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HRID 491914 반응식
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]([O:15][C:16]([NH:18][CH:19]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:22])=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:11]([O:15][C:16](=[O:17])[NH:18][CH:19]([C:20](=[O:22])[N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:23]([CH3:25])[CH3:24])([CH3:12])([CH3:13])[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 270655Boc-DL-valineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 67023731
[2-Methyl-1-(methyl-phenethyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of N-methyl-phenethyl-amine (2.2 mL, 15.3 mmol), 2-tert-butoxycarbonylamino-3-methyl-butyric acid (3.33 g, 15.3 mmol), HBTU (8.7 g, 22.95 mmol), DIPEA (6.1 mL, 33.7 mmol) and DMF (75 mL) was stirred at room temperature for 14 hours. To the resulting mixture was added sodium bicarbonate (400 mL) and the desired product was extracted with ethyl acetate (400 mL×2). The combined organic layers were washed with water, dried over MgSO4 and concentrated under reduced pressure to yield an oil. The oil was purified by column chromatography (50% EtOAc/heptane) to yield a residue.

후처리

  1. extractionthe desired product was extracted with ethyl acetate (400 mL×2)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto yield an oil
  6. customThe oil was purified by column chromatography (50% EtOAc/heptane)
  7. customto yield a residue

출처 및 근거

ORD 기록
ord-7c10d7dd65f843d0b5754a6184febf7c
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07531545B2

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