Hydrochloric Acid → Rac-5-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxazolidin-2-one

HRID 1640529ノート

反応式

HRID 1640529 の反応式
C([O:8][C:9](=O)[NH:10][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1)C1C=CC=CC=1.[C:22]([Si:26]([CH3:36])([CH3:35])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]1[CH2:34][O:33]1)([CH3:25])([CH3:24])[CH3:23].C(O[Li])(C)(C)C.C1COCC1.Cl>CN(C=O)C>[C:22]([Si:26]([CH3:35])([CH3:36])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]1[O:33][C:9](=[O:8])[N:10]([C:11]2[CH:20]=[CH:19][C:14]3[O:15][CH2:16][CH2:17][O:18][C:13]=3[CH:12]=2)[CH2:34]1)([CH3:23])([CH3:24])[CH3:25]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 13570755Rac-tert-butyl-dimethyl-(4-oxiranyl-butoxy)-silaneHCID 66736198(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-carbamic acid benzyl esterHCID 178506942HCID 178506942、化合物

生成物 1

HCID 66737368Rac-5-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxazolidin-2-one収率 82.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of (2,3-dihydro-benzo[1,4]dioxin-6-yl)-carbamic acid benzyl ester (0.75 g, 2.6 mmol) and rac-tert-butyl-dimethyl-(4-oxiranyl-butoxy)-silane (prepared according to Angew. Chem. (2007), 46, 5896; 0.91 g, 1.5 eq.) in DMF (8 mL) at 0° C. was treated with a 2.2M solution of t-BuOLi in THF (3.6 mL, 3 eq.). The mixture was stirred at rt for 22 h. HCl 1M (5.3 mL) was added and the mixture partitioned between EA and water. The org. phase was washed with water and brine, dried over MgSO4 and concentrated. The product was purified by FC (Hex/EA 1:1, 1:2) to give the title intermediate as a yellowish oil (0.87 g, 81% yield).

後処理

  1. customthe mixture partitioned between EA and water
  2. washphase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified by FC (Hex/EA 1:1, 1:2)

出典と根拠

ORDレコード
ord-d3852a30700c46a3a26e2e4a7ca013b5
出典データセット
uspto-grants-2012_02
特許番号
US08114867B2

反応ノート

読み込み中…