Water → (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid

HRID 1969573노트

반응식

HRID 1969573 반응식
P(=O)(O)(O)O.O.[CH2:7]([N:14]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:15]1[CH2:19][C@H:18]([C:20]([O-:22])=[O:21])[C@H:17]([CH3:23])[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1([C@H](N)C)C=CC=CC=1>CC(OC)(C)C>[CH2:24]([N:14]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C@@H:15]1[CH2:19][C@H:18]([C:20]([OH:22])=[O:21])[C@H:17]([CH3:23])[CH2:16]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 86761815(1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate.(R)-1-phenylethanamine

생성물 1

HCID 58557217(1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid수율 99.2%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

Phosphoric acid (11.40 mL, 196 mmol) was added to a flask containing water (500 mL). The solution was stirred for about 5 min. (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate•(R)-1-phenylethanamine (83 g, 187 mmol) was added to the solution in small portions. MTBE (500 mL) was added and the contents were mixed well, dissolving the solid. The phases were settled and separated. The aqueous layer was back extracted with MTBE (150 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid (60 g, 99%) as an oil: HPLC (Table 1, Method x) Rt=4.57 min.

후처리

  1. additionwas added to the solution in small portions
  2. additionthe contents were mixed well
  3. dissolutiondissolving the solid
  4. customseparated
  5. extractionThe aqueous layer was back extracted with MTBE (150 mL)
  6. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-02598564fd564f9a9f415a53d9c5ae82
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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