Water → 2-(4-Oxo-2-thioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid

HRID 63020

反応式

HRID 63020 の反応式
CO[C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[NH:10][CH2:11][C:12]([O-:14])=[O:13])=[O:4].[Na+].[S-:16][C:17]#[N:18].[Na+].O.Cl[Si](C)(C)C>CN1CCCC1=O>[O:4]=[C:3]1[NH:18][C:17](=[S:16])[N:10]([CH2:11][C:12]([OH:14])=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][C:5]1=2

参加物

6

反応物 4

HCID 962Water2 回HCID 6397ChlorotrimethylsilaneHCID 516871Sodium thiocyanateHCID 54675401Sodium ({2-[(Methyloxy)carbonyl]-1-cyclopenten-1-yl}amino)acetate

生成物 1

HCID 546754002-(4-Oxo-2-thioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid収率 83%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
117 °C

実験手順

Sodium ({2-[(Methyloxy)carbonyl]-1-cyclopenten-1-yl}amino)acetate (60 g) and sodium thiocyanate (26.6 g) were stirred in N-methylpyrrolidinone (240 ml) and water (2.94 ml) under a nitrogen atmosphere. Chlorotrimethylsilane (73.8 g) was added and the mixture heated to 117±3° C. After 3 hours at this temperature the reaction mixture was cooled to 90° C. and water (480 ml) was added. The mixture was cooled to 2° C. and the product isolated by filtration. It was washed with water (2×120 ml) then acetone (2×60 ml) and dried at 60° C. in an oven under reduced pressure to yield the title compound as an off-white solid (50.69 g, 83%). 1H NMR (d6 DMSO) δ 2.00 (2H, quintet), 2.60 (2H, t), 2.87 (2H, t), 4.95 (2H, broad s), 12.57 (1H, broad s), 13.26 (1H, broad s).

後処理

  1. temperatureAfter 3 hours at this temperature the reaction mixture was cooled to 90° C.
  2. temperatureThe mixture was cooled to 2° C.
  3. customthe product isolated by filtration
  4. washIt was washed with water (2×120 ml)
  5. dry with materialacetone (2×60 ml) and dried at 60° C. in an oven under reduced pressure

出典と根拠

ORDレコード
ord-f912f87dd4dd4749bc99fda8afbc7918
出典データセット
uspto-grants-2016_09
特許番号
US09447052B2

関連ノート

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