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

HRID 530578
ノート
印刷プレビュー

反応式

HRID 530578 の反応式
O[C@@H:2]([C:22]([CH3:25])([CH3:24])[CH3:23])[C@@H:3]([NH:7][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])[NH:7][C@H:3]2[C:4](=[O:6])[O:5][C@H:2]2[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86700020(2R*,3S*)-3-hydroxy-4,4-dimethyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid

生成物 1

HCID 867000285-phenylpentyl-N-[(2S*,3R*)-2-tert-butyl-4-oxo-oxetan-3-yl]-carbamate収率 38.3%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

Under nitrogen atmosphere, to a stirred mixture of (2R*,3S*)-3-hydroxy-4,4-dimethyl-2-(5-phenyl-pentoxy-carbonylamino)-pentanoic acid (0.346 g, 0.98 mmol) in dry CH2Cl2 (45 mL), at 0° C., Et3N (0.41 mL, 2.95 mmol) and subsequently TBTU (0.38 g, 1.20 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. The organics were then removed under reduced pressure, and the resulting crude product purified by column chromatography, using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (from 90:10 to 70:30) to afford the pure title compound (0.125 g, 38%), as white solid. MS (ESI) m/z: 351 [M−NH4]+; (ESI) m/z: 332 [M−H]−. 1H NMR (DMSO-d6) δ 0.93 (s, 9H), 1.34 (h, J=6.37, 7.16 Hz, 2H), 1.53-1.65 (m, 4H), 2.57 (t, J=7.69 Hz, 2H), 4.02 (q, J=6.25 Hz, 2H), 4.36 (d, J=6.24 Hz, 1H), 5.56 (dd, J=6.32, 8.47 Hz, 1H), 7.07-7.34 (m, 5H), 8.38 (d, J=8.48 Hz, 1H).

後処理

  1. waitThe mixture was left
  2. customThe organics were then removed under reduced pressure
  3. customthe resulting crude product purified by column chromatography
  4. washeluting with Cy

出典と根拠

ORDレコード
ord-16e73e96b3274093a93b30316fda39c7
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09353075B2

反応ノート

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