Triethylamine → 5-phenylpentyl-N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530532ノート

反応式

HRID 530532 の反応式
O[C@@H:2]([CH3:23])[C@@H:3]([N:7]([CH3:22])[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:9])[C:4]([OH:6])=[O:5].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:8](=[O:9])[N:7]([CH3:22])[C@H:3]2[C:4](=[O:6])[O:5][C@H:2]2[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 73294311(2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid

生成物 1

HCID 732943125-phenylpentyl-N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate収率 23.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred mixture of (2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid (0.04 g, 0.14 mmol) in dry CH2Cl2(5.0 mL), under nitrogen atmosphere at 0° C., Et3N (0.06 mL, 0.41 mmol) and subsequently TBTU (0.05 g, 0.17 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. Upon full conversion of the starting material, the organics were removed under reduced pressure, and the resulting crude product absorbed over silica gel and purified by column chromatography, eluting with Cy:EtOAc (from 100:0 to 0:100) to afford the title compound (0.01 g, 23%), as a mixture of two rotamers (1:1.5 ratio), as a colorless oil. [α]25D −16.66 (c 0.1, CHCl3). 1H NMR (DMSO-d6) δ 1.29-1.41 (m, 10H), 1.53-1.69 (m, 8H), 2.58 (t, J=7.6 Hz, 4H), 2.93 (s, 6H), 3.98-4.11 (m, 4H), 4.77-4.89 (m, 2H), 5.24-5.33 (m, 1H, major rotamer), 5.35-5.43 (m, 1H, minor rotamer), 7.13-7.32 (m, 10H).

後処理

  1. waitThe mixture was left
  2. customUpon full conversion of the starting material, the organics were removed under reduced pressure
  3. customthe resulting crude product absorbed over silica gel
  4. custompurified by column chromatography
  5. washeluting with Cy

出典と根拠

ORDレコード
ord-884e41c8730540169c11338bb228b64b
出典データセット
uspto-grants-2016_05
特許番号
US09353075B2

反応ノート

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