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Methylamine → N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester

HRID 366174
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HRID 366174 반응식
[C:1]([O:5][C:6]([N:8]([CH3:20])[C@@H:9]([C:17](O)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:23]1[C:27]2C=CC=CC=2N=N1.CN.C(Cl)Cl>CN(C)C=O.CO.O>[C:1]([O:5][C:6](=[O:7])[N:8]([CH3:20])[C@@H:9]([C:17](=[O:18])[NH:23][CH3:27])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

8

반응물 4

HCID 6329MethylamineHCID 6344DichloromethaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 7015127N-Boc-N-methyl-D-phenylalanine

생성물 1

HCID 10613603N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester수율 108%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

N-Tert-butoxycarbonyl-N-methyl-D-phenylalanine (1.22 g, 4.4 mmol), 1-hydroxybenzotriazole hydrate (0.59 g, 4.4 mmol) and 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimid hydrochloride (0.88 g, 4.6 mmol) were dissolved in N,N-dimethylformamide (25 mL) and stirred for 30 min. Methylamine (0.51 g of a 40% solution in methanol, 6.6 mmol) was added and the mixture was stirred overnight. Methylene chloride (80 mL) and water (100 mL) were added and the phases were separated. The organic phase was washed with sodium hydroxide (20 mL, 1 N), sodium hydrogensulfate (50 mL, 10%) and water (50 mL). The organic phase was dried (magnesium sulfate) and the solvent removed in vacuo to afford 1.39 g of N-methyl-N-((R)1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester.

후처리

  1. stirringthe mixture was stirred overnight
  2. customthe phases were separated
  3. washThe organic phase was washed with sodium hydroxide (20 mL, 1 N), sodium hydrogensulfate (50 mL, 10%) and water (50 mL)
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-52e2428165dc4c12af8fd94316e3bbce
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06127391

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