(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate → (1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acid

HRID 2179728노트

반응식

HRID 2179728 반응식
[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([O:11]CC2C=CC=CC=2)=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([OH:11])=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]

참가 물질

4

반응물 1

HCID 86650107(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate

생성물 1

HCID 11183048(1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acid수율 54.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A stirred solution of (1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate (0.650 g, 2.36 mmol) in EtOAc (10 ml) at room temperature, 10% Pd/C (catalytic amount) were added and the reaction mixture was stirred under H2 gas atmosphere at room temperature for about 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through celite bed. The obtained filtrate was concentrated under reduced pressure to afford title compound as an off white solid. Wt: 0.240 g; Yield: 54.9%; 1H NMR (300 MHZ, CD3OD): δ 8.09 (d, J=3.0 Hz, 1H), 4.08-3.96 (m, 1H), 2.62-2.58 (m, 1H), 2.20-2.15 (m, 2H), 1.93 (s, 3H), 1.26 (s, 3H), 0.92 (s, 3H); Mass: [M+1]+ 186 (70%), [M+Na]+ 208 (93%). IR (KBr, cm−1): 3349, 2962, 1697, 1624, 1557, 1428, 1377, 1257, 1075, 988, 920, 736; M.R: 194.7° C.-216.2° C.

후처리

  1. customAfter completion of the reaction (monitored by TLC)
  2. filtrationthe reaction mixture was filtered through celite bed
  3. concentrationThe obtained filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-36ff39b084814270ae1bb442be98ed00
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067966B2

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