Hydrochloric Acid → 3-(9H-fluoren-9-ylmethoxycarbonylamino)cyclohexane-1-carboxylic Acid

HRID 1352045

반응식

HRID 1352045 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.C(=O)([O-])O.[Na+].[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31](ON3C(=O)CCC3=O)=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.Cl>O.O1CCCC1>[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([NH:1][CH:2]3[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]3)=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 5448873-Aminocyclohexanecarboxylic acid

생성물 1

HCID 42601103-(9H-fluoren-9-ylmethoxycarbonylamino)cyclohexane-1-carboxylic Acid수율 57%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

3-Aminocyclohexanecarboxylic acid (10 g, 70 mmol) was added to a solution of sodium hydrogen carbonate (7.6 g, 91 mmol) in water (100 mL). A solution of 1-[[(9H-fluoren-9-ylmethoxy)carbonyl]oxy-2,5-pyrrolidinedione (Fmoc-OSu; 28.3 g, 84 mmol) in tetrahydrofuran (200 mL) was added. The solution was stirred at room temperature overnight and then poured into 3 M HCl (200 mL). The mixture was extracted with ethyl acetate (100 mL then 50 mL) and the combined organic layers were washed with saturated brine (3×100 mL), dried (Na2SO4), filtered, and concentrated to approximately 200 mL. Crystallization occurred on concentration. The mixture was allowed to stand overnight, then the solid was filtered off, washed with ethyl acetate and dried in a vacuum oven at 55° C. to give 3-[N-[(9H-fluoren-9-ylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid (14.66, 57%) as a white solid.

후처리

  1. extractionThe mixture was extracted with ethyl acetate (100 mL
  2. wash50 mL) and the combined organic layers were washed with saturated brine (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to approximately 200 mL
  6. customCrystallization
  7. concentrationoccurred on concentration
  8. waitto stand overnight
  9. filtrationthe solid was filtered off
  10. washwashed with ethyl acetate
  11. customdried in a vacuum oven at 55° C.

출처 및 근거

ORD 기록
ord-ca089e05d12a4d33a94b1fd48ac172a1
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217728B2

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