Triphenylphosphine → HCID 86731260、化合物

HRID 2277199ノート

反応式

HRID 2277199 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([F:12])=[CH:10][C:9]([C:13]3[O:14][C:15]4[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:8][C:7]=2[F:23])[CH2:3][CH2:2]1.O[CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([F:12])=[CH:10][C:9]([C:13]3[O:14][C:15]4[CH:21]=[C:20]([O:22][CH2:27][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH3:25])[CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:8][C:7]=2[F:23])[CH2:2][CH2:3]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 66880968DIAD tolueneHCID 867312582-(4-(Cyclopropylmethoxy)-3,5-difluorophenyl)-1,3-benzoxazol-6-ol

生成物 1

HCID 86731260HCID 86731260、化合物収率 90.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(4-(cyclopropylmethoxy)-3,5-difluorophenyl)-1,3-benzoxazol-6-ol (1.92 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.59 g) and triphenylphosphine (2.38 g) in THF (15 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 4.78 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (2.60 g). 1H NMR (300 MHz, CDCl3) δ 0.29-0.37 (2H, m), 0.56-0.67 (2H, m), 1.17-1.36 (4H, m), 1.46 (9H, s), 3.94-4.19 (5H, m), 4.67-4.82 (1H, m), 6.97 (1H, dd, J=8.7, 2.3 Hz), 7.10 (1H, d, J=2.3 Hz), 7.62 (1H, d, J=8.7 Hz), 7.68-7.81 (2H, m).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-eed1d9b4a77e489c9a72b4943649c11d
出典データセット
uspto-grants-2015_09
特許番号
US09133129B2

反応ノート

読み込み中…