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Triethylamine → tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

HRID 68379
ノート
印刷プレビュー

反応式

HRID 68379 の反応式
[Br:1][C:2]1[C:3]([F:21])=[CH:4][C:5]([F:20])=[C:6]([C@:8]23[CH2:16][O:15][C@H:14]([CH2:17][F:18])[C@H:13]2[CH2:12][S:11][C:10]([NH2:19])=[N:9]3)[CH:7]=1.[O:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O.CCN(CC)CC>C1COCC1>[Br:1][C:2]1[C:3]([F:21])=[CH:4][C:5]([F:20])=[C:6]([C@:8]23[CH2:16][O:15][C@H:14]([CH2:17][F:18])[C@H:13]2[CH2:12][S:11][C:10]([NH:19][C:23](=[O:22])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:9]3)[CH:7]=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 90495Di-tert-butyl dicarbonateHCID 86707818(4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

生成物 1

HCID 86707819tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
100 °C

実験手順

(4aS,5S,7aS)-7a-(5-Bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (620 mg, 1.63 mmol) was dissolved in THF (10 mL). (BOC)2O (0.45 mL, 1.95 mmol) and Et3N (0.27 mL, 1.95 mmol) were added and the reaction was stirred at 100° C. After 1 hour, the solvents were removed in vacuo. The residue was purified using column chromatography (Biotage SNAP 25 g, 20 mL/min eluting with 20-80% EtOAc in n-hexane) to leave the title compound as a foam. (704 mg). 1H NMR (400 MHz, CDCl3) δ ppm: 7.54 (t, J=1.00 Hz, 1H), 6.86-7.01 (m, 1H), 4.49-4.71 (m, 3H), 4.45 (dd, J=1.22, 8.56 Hz, 1H), 3.68-3.92 (m, 1H), 2.95-3.20 (m, 2H), 2.73 (t, J=1.00 Hz, 1H), 1.46-1.64 (m, 9H)

後処理

  1. customthe solvents were removed in vacuo
  2. customThe residue was purified
  3. washcolumn chromatography (Biotage SNAP 25 g, 20 mL/min eluting with 20-80% EtOAc in n-hexane)

出典と根拠

ORDレコード
ord-3eba5390d71a4500af497243a052647f
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822455B2

反応ノート

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