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Ethyl trifluoroacetate → (1R,3S,4S)-3-[(2,2,2-Trifluoro-acetylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 882796
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HRID 882796 반응식
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[C:10]([O:14][C:15]([N:17]1[C@H:22]([CH2:23][NH2:24])[C@@H:21]2[CH2:25][C@H:18]1[CH2:19][CH2:20]2)=[O:16])([CH3:13])([CH3:12])[CH3:11].CCN(C(C)C)C(C)C>C1COCC1>[C:10]([O:14][C:15]([N:17]1[C@H:22]([CH2:23][NH:24][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[C@@H:21]2[CH2:25][C@H:18]1[CH2:19][CH2:20]2)=[O:16])([CH3:13])([CH3:11])[CH3:12]
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참가 물질

5

반응물 3

HCID 9794Ethyl trifluoroacetateHCID 81531DiisopropylethylamineHCID 66866957tert-butyl (1R,3S,4S)-3-(aminomethyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

생성물 1

HCID 86649700(1R,3S,4S)-3-[(2,2,2-Trifluoro-acetylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

Ethyl trifluoroacetate (12.2 mmol, 1.30 eq) is added to a solution of (1R,3S,4S)-3-aminomethyl-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (9.42 mmol, 1.00 eq) and DIPEA (14.1 mmol, 1.50 eq) in THF (25 mL). After 50 min the mixture is concentrated in vacuo, diluted with TBME (100 mL) and washed twice with aq. citric acid (5%) and water respectively. The organic layer is dried over MgSO4 and concentrated in vacuo to give a crude product which is used without further purification. LC-MS (basic): tR=0.95 min; [M+H]+=323.2.

후처리

  1. concentrationAfter 50 min the mixture is concentrated in vacuo
  2. additiondiluted with TBME (100 mL)
  3. washwashed twice with aq. citric acid (5%) and water respectively
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f3b1a520da93430fac43de711a19aa10
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08236801B2

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