(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester → (2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid

HRID 429124노트

반응식

HRID 429124 반응식
C([O:8][C:9](=[O:25])[C@@H:10]([NH:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>C1COCC1.[Pd]>[N:18]1([C:16]([NH:15][C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:25])=[O:8])=[O:17])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

참가 물질

4

반응물 1

HCID 10593708(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

생성물 1

HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid수율 93.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester (38.5 g, 111 mmol) in 600 mL of THF was hydrogenated at 50 psi over 20% Pd/C (2.00 g) for 17 minutes. The reaction mixture was filtered through celite and concentrated to dryness. The residue was heated in 50 mL of hexane. The resulting suspension was cooled, and the solid was collected by filtration and washed with hexane. The solid was dried at room temperature under vacuum to give (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid as a white solid (26.6 g, 93%); mp 88-89° C.

후처리

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated to dryness
  3. temperatureThe residue was heated in 50 mL of hexane
  4. temperatureThe resulting suspension was cooled
  5. filtrationthe solid was collected by filtration
  6. washwashed with hexane
  7. customThe solid was dried at room temperature under vacuum

출처 및 근거

ORD 기록
ord-7b382acd046c4ea3bccd4708b2803601
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316440B1

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