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Hydrochloric Acid → tert-Butyl 2-methyl-4-morpholino-4-oxobutan-2-ylcarbamate

HRID 632018
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HRID 632018 반응식
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.Cl>C(Cl)Cl>[CH3:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH2:10][C:11]([N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1)=[O:13])[CH3:15]
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참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acid

생성물 1

HCID 71105557
tert-Butyl 2-methyl-4-morpholino-4-oxobutan-2-ylcarbamate
수율 59.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(tert-Butoxycarbonylamino)-3-methylbutanoic acid (2.7 g, 12.4 mmol), HBTU (CAN 94790-37-1, 6.1 g, 16.1 mmol) and triethylamine (CAN 121-44-8, 2.5 g, 24.8 mmol) was added to a solution of morpholine (CAN 110-91-8, 2.2 g, 24.8 mmol) in methylene chloride (50 mL). The mixture was stirred overnight at room temperature. Aqueous hydrochloride (1 N, 50 mL) was added, and the mixture extracted with methylene chloride. The organic extracts were washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (silica gel, 50 g, eluting with 30% ethyl acetate in petroleum ether) to give the product (2.1 g, 59%); MS (EI): m/e 287.1 [M+H]+.

후처리

  1. extractionthe mixture extracted with methylene chloride
  2. washThe organic extracts were washed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica gel, 50 g, eluting with 30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-7cb1764fd4fe4a40989c54f59a025917
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321727B2

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