Triethylamine → (4S)-4-Isobutyl-5,5-diphenyl-2-oxazolidinone

HRID 1246385ノート

反応式

HRID 1246385 の反応式
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C@@H:10]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:25]([C@H:10]1[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:12][C:2](=[O:3])[NH:9]1)[CH:26]([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 10945486(S)-(-)-2-Amino-4-methyl-1,1-diphenyl-1-pentanol

生成物 1

HCID 9904230(4S)-4-Isobutyl-5,5-diphenyl-2-oxazolidinone収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trichloromethyl chloroformate (13.0 g, 65.8 mmol) was added to a mixture of (S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol 16 (12.4 g of 65%, 29.9 mmol) and triethylamine (12.7 g, 125.5 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred for 15 h, allowing to warm to room temperature. The mixture was then washed with HCl (3×200 ml) and water (2×200 ml), and dried over MgSO4. Concentration gave a crude product, which was washed with diethyl ether to afford the title compound 17 (7.9 g, 90%) as a white solid. m.p. 212–214° C. [α]D25=−286.1° (c, 4.32 in CHCl3). δH 0.85 (3H, d, J=6.6 Hz, CH3), 0.91 (3H, d, J=6.6 Hz, CH3), 0.96–1.08 (2H, m, CH2), 1.53–1.73 (1H, m, CH—Me2), 4.57 (1H, dd, J=10.5 and 3.60 Hz, CH—NH), 7.05 (1H, s, NH), 7.16–7.50 (10H, m, Ar—H). δC 20.8, 23.7, 24.9, 41.8, 58.8, 89.1, 125.9, 126.3, 127.6, 127.8, 128.1, 128.3, 139.3, 142.5 (Ar), 158.8 (C═O). νmax (cm−1): 3261, 3160 (N—H), 2955, 2869 (methyl and methylene C—H), 1752, 17235 (C═O), 1495, 1447 (Ar C═C), 1251 (C—O). m/e 313 (MNH4+, 12%), 296 (MH+, 15%), 237 (100%).

後処理

  1. washThe mixture was then washed with HCl (3×200 ml) and water (2×200 ml)
  2. dry with materialdried over MgSO4
  3. concentrationConcentration
  4. customgave a crude product, which
  5. washwas washed with diethyl ether

出典と根拠

ORDレコード
ord-731cc67f5f344e1898cf0d9a8ccccd25
出典データセット
uspto-grants-2006_10
特許番号
US07126028B1

反応ノート

読み込み中…