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Methyl N-(triethylammoniosulfonyl)carbamate → 2-[4-(N-tert-butoxycarbonylamino-methyl)-phenyl]-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

HRID 2221438
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HRID 2221438 반응식
[C:1]([NH:8][CH2:9][C:10]1[CH:25]=[CH:24][C:13]([C:14]([NH:16][CH:17]([CH2:22]O)[C:18]([O:20][CH3:21])=[O:19])=[O:15])=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[C:1]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]2[O:15][CH2:22][CH:17]([C:18]([O:20][CH3:21])=[O:19])[N:16]=2)=[CH:24][CH:25]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
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참가 물질

4

반응물 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 69202136HCID 69202136, 화합물

생성물 1

HCID 692000722-[4-(N-tert-butoxycarbonylamino-methyl)-phenyl]-4,5-dihydro-oxazole-4-carboxylic acid methyl ester수율 97.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of methyl 2-[4-(N-Boc-aminomethyl)benzoylamino]-3-hydroxypropionate (32.0 g, 90.8 mmol) in THF (150 ml) was added Burgess' Reagent (26.0 g, 109 mmol) and 3 Å molecular sieves (1 g). The reaction was allowed to stir at 60° C. for 2 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude product was dissolved in dichloromethane and purified by flash chromatography over silica gel with ethyl acetate/dichloromethane (1/1) to give methyl 2-[4-(N-Boc-aminomethyl)-phenyl]-4,5-dihydrooxazol-4-ylcarboxylate (29.5 g, 88.2 mmol) as a pale tan oil.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude product was dissolved in dichloromethane
  4. custompurified by flash chromatography over silica gel with ethyl acetate/dichloromethane (1/1)

출처 및 근거

ORD 기록
ord-61f5c48fac01495a985ffb234dd91d0d
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07368572B2

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