Ethanethiol → 2-Hydroxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3, 2-a]pyridin-8-yl]-amide

HRID 1259389ノート

反応式

HRID 1259389 の反応式
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([CH:25]2[CH2:27][CH:26]2[CH2:28][O:29]CC2C=CC=CC=2)(=[O:24])=[O:23])=[C:12]2[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16].B(F)(F)F.C(S)C>C(OC(=O)C)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([CH:25]2[CH2:27][CH:26]2[CH2:28][OH:29])(=[O:24])=[O:23])=[C:12]2[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16]

参加物

5

反応物 3

HCID 6343EthanethiolHCID 6356Boron trifluorideHCID 583805532-Benzyloxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

生成物 1

HCID 529340922-Hydroxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3, 2-a]pyridin-8-yl]-amide収率 27%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

2-Benzyloxymethyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide (0.05 g, 0.0001 mol) was added to a stirred solution of BF3.EtO2 (0.34 g, 0.002 mol) in ethane thiol (0.05 g, 0.001 mol) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was quenched with saturated NaHCO3 solution and extracted with ethylacetate. The organic layer was washed with water, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (2-3% MeOH in DCM) afforded 11 mg of the product (27% yield).

後処理

  1. customat 0° C.
  2. customThe reaction mixture was quenched with saturated NaHCO3 solution
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (2-3% MeOH in DCM)

出典と根拠

ORDレコード
ord-d3373bbbd136424d8e303cf0efc5270f
出典データセット
uspto-grants-2013_06
特許番号
US08466289B2

反応ノート

読み込み中…