Imidazole → (S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1986683ノート

反応式

HRID 1986683 の反応式
O[CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I>C(Cl)(Cl)Cl>[I:41][CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15]

参加物

6

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68915929(S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

生成物 1

HCID 68912224(S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one収率 80%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

The compound (S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (108LM26-23) (2.52 g, 11.4 mmol), triphenylphosphine (6.12 g, 23.3 mmol), imidazole (1.98 g, 29.1 mmol) and iodine (8.88 g, 35.0 mmol) in CHCl3 (30 mL) were reacted according to GP4 to give the title compound (108LM27-24) (3.02 g, 80%). 1H NMR (CDCl3) δ 7.07-7.00 (m, 4H), 4.65-4.55 (m, 2H), 3.94 (dd, J=1.7 Hz, J=6.7 Hz, CH2), 3.23-3.14 (m, 2H), 2.18-2.07 (m, 1H), 1.05 (d, J=6.1 Hz, CH3).

出典と根拠

ORDレコード
ord-bcc5464e0a41400a808b69cdb71ed3dd
出典データセット
uspto-grants-2009_06
特許番号
US07550459B2

反応ノート

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