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Water → methyl (2S,4R)-4-(2-benzoxazolyl)amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate

HRID 1791889
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HRID 1791889 반응식
[NH2:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.C(N(CC)CC)C.Cl[C:26]1[O:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.O>O1CCCC1>[O:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[NH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 70099181-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

생성물 1

HCID 69754879methyl (2S,4R)-4-(2-benzoxazolyl)amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Methyl (2S,4R)-4-amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate [product of Reference Example 4(2), 3.32 g] and triethylamine (1.4 mL) were dissolved in tetrahydrofuran (20 mL). 2-Chlorobenzoxazole (0.86 mL) was added thereto and the mixture was stirred at room temperature for 48 hr. The reaction mixture was added to water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution and brine, and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography to give methyl (2S,4R)-4-(2-benzoxazolyl)amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate (1.48 g) as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-12c1e64ab7074546a3d625ad998258d9
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07074794B2

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