(S)-2-((S)-1-tert-butoxycarbonyl-ethylamino)-3-(2',5'-dichloro-biphenyl-4-yl)-propionic acid benzyl ester → (S)-2-((S)-1-tert-butoxycarbonyl-ethylamino)-3-(2',5'-dichloro-biphenyl-4-yl)-propionic acid

HRID 388875ノート

反応式

HRID 388875 の反応式
C([O:8][C:9](=[O:36])[C@@H:10]([NH:26][C@H:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[Cl:25])=[CH:14][CH:13]=1)C1C=CC=CC=1>CCOC(C)=O.CO.[Pd]>[C:32]([O:31][C:29]([C@@H:27]([NH:26][C@@H:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[Cl:25])=[CH:16][CH:17]=1)[C:9]([OH:36])=[O:8])[CH3:28])=[O:30])([CH3:33])([CH3:34])[CH3:35]

参加物

5

反応物 1

HCID 58280524(S)-2-((S)-1-tert-butoxycarbonyl-ethylamino)-3-(2',5'-dichloro-biphenyl-4-yl)-propionic acid benzyl ester

生成物 1

HCID 58280551(S)-2-((S)-1-tert-butoxycarbonyl-ethylamino)-3-(2',5'-dichloro-biphenyl-4-yl)-propionic acid収率 90.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Step 4′: A suspension of (S)-2-((S)-1-tert-Butoxycarbonyl-ethylamino)-3-(2′,5′-dichloro-biphenyl-4-yl)-propionic acid benzyl ester (580 mg, 1.10 mmol) and 5% Pd on carbon (0.146 g) in EtOAc (10 mL) was treated with H2 (balloon) and stirred at rt for 1.5 hour. The resulted precipitate was dissolved in methanol and filtered through celite pad. The filtrate was concentrated under reduced pressure and the obtained residue was re-crystallized from EtOAc to give (S)-2-((S)-1-tert-butoxycarbonyl-ethylamino)-3-(2′,5′-dichloro-biphenyl-4-yl)-propionic acid (438 mg). 1H NMR (400 MHz, DMSO-d6) δ 1.12 (d, 3H, J=7.1 Hz), 1.35 (s, 9H), 2.84 (dd, 2H, J=7.3, 13.6 Hz), 2.95 (dd, 2H, J=6.1, 13.6 Hz), 3.20 (dd, 1H, J=6.8, 13.6 Hz), 3.48 (dd, 1H, J=6.1, 7.3 Hz), 7.33 (d, 2H, J=8.6 Hz), 7.37 (d, 2H, J=8.3 Hz), 7.42-7.49 (m, 2H), 7.60 (d, 2H, J=8.6 Hz); MS: m/z (MH+) 438.

後処理

  1. additionwas treated with H2 (balloon)
  2. filtrationfiltered through celite pad
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe obtained residue was re-crystallized from EtOAc

出典と根拠

ORDレコード
ord-ae5937baef494182a6d7f19fdf28df63
出典データセット
uspto-grants-2013_02
特許番号
US08377978B2

反応ノート

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