1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl(S)-1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-ylcarbamate

HRID 919594노트

반응식

HRID 919594 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:36][C:37]1[CH:38]=[C:39]([NH:44][CH2:45][C:46](O)=[O:47])[CH:40]=[C:41]([Cl:43])[CH:42]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:36][C:37]1[CH:38]=[C:39]([NH:44][CH2:45][C:46]([N:1]2[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]2)=[O:47])[CH:40]=[C:41]([Cl:43])[CH:42]=1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 13138167(3,5-Dichlorophenyl)glycine

생성물 1

HCID 69676426tert-butyl(S)-1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-ylcarbamate수율 98%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of tert-butyl(S)-piperidin-3-ylcarbamate (500 mg, 2.5 mmol), in DMF (5 mL) was added EDCI (573 mg, 3.0 mmol), HOBt (405 mg, 3.0 mmol), 2-(3,5-dichlorophenylamino)acetic acid (550 mg, 2.5 mmol) and DIEA (0.5 mL, 3.0 mmol) at 0° C. The reaction mixture was stirred at rt overnight, the reaction mixture was diluted with EtOAc and washed with water. The water layer was extracted with the EtOAc and the combined organic layer was dried over Na2SO4 and evaporated in vacuo to give the crude compound that was purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (900 mg, 98%) of the titled intermediate. LCMS: m/z: [M+1]=402.

후처리

  1. washwashed with water
  2. extractionThe water layer was extracted with the EtOAc
  3. dry with materialthe combined organic layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customto give the crude compound that
  6. customwas purified by column chromatography (silica gel, gradient MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-86850e8ba64545f0ad05abdb7aac3483
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273028B2

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