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Hydrochloric Acid → (2S,5R)-5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl) piperidine-2-carboxylic acid

HRID 870869
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HRID 870869 반응식
O[Li].O.[CH2:4]([O:11][N:12]([C@H:25]1[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:28]([C:38]([O:40]CC)=[O:39])[CH2:27][CH2:26]1)[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])(=[O:15])=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C1COCC1.O>[CH2:4]([O:11][N:12]([C@H:25]1[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[C@H:28]([C:38]([OH:40])=[O:39])[CH2:27][CH2:26]1)[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])(=[O:14])=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86700664(2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate

생성물 1

HCID 86700669(2S,5R)-5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl) piperidine-2-carboxylic acid수율 95.7%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

LiOH.H2O (2.7 g, 64 mmol) was added to a solution of (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate (9.0 g, 16 mmol) in THF (60 mL) and H2O (60 mL) at rt. The mixture was stirred at rt for 36 hrs., then the reaction mixture was adjusted to pH 4 with 1N HCl, and extracted with EtOAc (3×). The combined organic layer was washed with saturated sodium chloride, dried over Na2SO4 and concentrated to give (2S,5R)-5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (8.2 g, 95%) as a yellow solid. ESI-MS (EI+, m/z): 558 [M+Na]+.

후처리

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layer was washed with saturated sodium chloride
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9e5070df3eb044ec816b5f5b7745d54b
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969570B2

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