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

HRID 530559ノート

反応式

HRID 530559 の反応式
O[C@H:2]([CH:22]([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].O[C@@H](C(C)C)[C@@H](NC(OCCCCCC1C=CC=CC=1)=O)C(O)=O.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[CH:22]([CH3:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86700000(2R*,3S*)-3-hydroxy-4-methyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acidHCID 86700002(2R*,3R*)-3-hydroxy-4-methyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid

生成物 1

HCID 867000015-phenylpentyl-N-[(2R*,3R*)-2-isopropyl-4-oxo-oxetan-3-yl]-carbamate収率 56%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-3-hydroxy-4-methyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid and (2R*,3S*)-3-hydroxy-4-methyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid (0.076 g, 0.24 mmol) in dry CH2Cl2 (10.0 mL), at 0° C., Et3N (0.2 mL, 1.44 mmol) and subsequently TBTU (0.091 g, 0.28 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 100:0 to 80:20) to afford the pure title compound (0.041 g, 56%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 337 [M−NH4]+; (ESI) m/z: 318 [M−H]−. 1H NMR (DMSO-d6) δ 0.87 (d, J=6.75 Hz, 3H), 0.95 (d, J=6.55 Hz, 3H), 1.27-1.43 (m, 2H), 1.49-1.69 (m, 4H), 1.87-2.08 (m, 1H), 2.57 (t, J=7.67 Hz, 2H), 3.99 (t, J=6.59 Hz, 2H), 4.22 (dd, J=4.39, 9.13 Hz, 1H), 4.73 (dd, J=4.40, 8.18 Hz, 1H), 7.10-7.35 (m, 5H), 8.06 (d, J=8.16 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-112fd976d4484569b28be01abaab16d4
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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