Phosphoric Acid → 5-[(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-thiophene-3-carboxylic acid methyl ester

HRID 1792884ノート

反応式

HRID 1792884 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@:13]3([N:17]([CH3:18])[C:16](=[O:19])[N:15]([C:20]4[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=4)[C:14]3=[O:28])[CH2:12][N:11]([CH2:29][C:30]3[S:34][CH:33]=[C:32]([C:35]([OH:37])=[O:36])[CH:31]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[CH3:38][Si](C=[N+]=[N-])(C)C.OP(O)(O)=O>C(Cl)Cl.CO.O.CO>[CH3:38][O:36][C:35]([C:32]1[CH:31]=[C:30]([CH2:29][N:11]2[CH2:10][C@@H:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[C@:13]3([N:17]([CH3:18])[C:16](=[O:19])[N:15]([C:20]4[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=4)[C:14]3=[O:28])[CH2:12]2)[S:34][CH:33]=1)=[O:37]

参加物

7

反応物 3

HCID 1004Phosphoric Acid2 回HCID 167693TrimethylsilyldiazomethaneHCID 11635371Bms-587101

生成物 1

HCID 510719905-[(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-thiophene-3-carboxylic acid methyl ester

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒2 回HCID 21226129Dichloromethane methanol溶媒

実験手順

To a solution of 5-[(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-thiophene-3-carboxylic acid (example 37) (0.150 g, 0.27 mmol) in DCM/MeOH (5:1 mL) was added trimethylsilyldiazomethane (2.0 M solution in hexane, 0.33 mL, 0.67 mmol) over a period of three minutes at RT. The reaction mixture was stirred at RT for twenty minutes, quenched by the slow addition of acetic acid (approximatly ten drops) and partitioned between DCM (20 mL) and saturated aqueous sodium bicarbonate (15 mL). The DCM layer was washed with brine (20 mL), dried over sodium sulfate and concentrated to yield a thick oil. LC retention time=3.34 min. Column used: YMC S5 combiscreen ODS 4.6×50 mm (4 min. gradient); Solvent A=10% MeOH, 90% H2O and 0.2% H3PO4; solvent B=90% MeOH, 10% H2O, 0.2% H3PO4.

後処理

  1. customquenched by the slow addition of acetic acid (approximatly ten drops) and
  2. custompartitioned between DCM (20 mL) and saturated aqueous sodium bicarbonate (15 mL)
  3. washThe DCM layer was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto yield a thick oil
  7. customYMC S5 combiscreen ODS 4.6×50 mm (4 min. gradient)

出典と根拠

ORDレコード
ord-00de50691c634edaa9e1945831f94a76
出典データセット
uspto-grants-2006_07
特許番号
US07078420B2

反応ノート

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