Sodium Iodide → HCID 10282284、化合物

HRID 895794ノート

反応式

HRID 895794 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].[CH3:11][C@@H:12]1[O:22][C:20](=[O:21])[C@@H:19]([NH:23][C:24]([C:26]2[C:31]([OH:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)=[O:25])[CH2:18][O:17][C:15](=[O:16])[C@H:14]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:13]1[O:42][C:43]([CH:45]([CH3:47])[CH3:46])=[O:44].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(Cl)Cl>[CH3:46][CH:45]([CH3:47])[C:43]([O:42][C@@H:13]1[C@@H:14]([CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:15](=[O:16])[O:17][CH2:18][C@H:19]([NH:23][C:24]([C:26]2[C:31]([O:32][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)=[O:25])[C:20](=[O:21])[O:22][C@H:12]1[CH3:11])=[O:44]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 468590(3S,6S,7R,8R)-3-[[(3-Hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl 2-methylpropanoate

生成物 1

HCID 10282284HCID 10282284、化合物収率 81.4%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

実験手順

Benzyl bromide (0.233 mol, 27.7 mL) was added to a solution of NaI (0.097 mol, 14.5 g) in acetone (1 L). Natural product UK-2A (1) (0.194 mol, 100 g) was added followed by powdered K2CO3 (0.388 mol, 53 g) and the mixture stirred vigorously overnight. The mixture was diluted with CH2Cl2 (500 mL) and washed with H2O (2×500 mL). The organic layer was dried (MgSO4), and concentrated in vacuo. Recrystallization (EtOAc/hexane) gave 95.5 g (79%) of 2 as an off-white solid (m.p. 169-170° C.) which contained ˜6.5% N-benzylated product (LC-MS). 1H-NMR and MS (M+1 605) were consistent for the title compound (2). The compound was used in the next step without further purification. The N-benzylated by-product could be removed from the mixture prior to recrystallization by filtration of the crude reside through a plug of silica gel (30% acetone/hexane as the eluent).

後処理

  1. washwashed with H2O (2×500 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customRecrystallization (EtOAc/hexane)

出典と根拠

ORDレコード
ord-c8eb4abe5cf34cc28168619f147843dd
出典データセット
uspto-grants-2005_07
特許番号
US06916932B2

反応ノート

読み込み中…