Acetic Acid → HCID 22310861、化合物

HRID 967105ノート

反応式

HRID 967105 の反応式
C([BH3-])#N.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:20]([O:22][CH3:23])=[O:21].[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=O.C(O)(=O)C>CO>[Cl:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH2:29][C:28]([O:32][CH2:33][CH3:34])=[O:31])=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:20]([O:22][CH3:23])=[O:21]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydrideHCID 22310882HCID 22310882、化合物

生成物 1

HCID 22310861HCID 22310861、化合物収率 67%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium cyanoborohydride (0.2 g) was added in a single portion to methyl N-(3,4-dichlorobenzyl)-5-aminoindole-2-carboxylate (0.16 g), ethyl glyoxalate (0.2 ml of 50 wt % solution in toluene) and acetic acid (0.1 ml) in methanol (3 ml). The reaction was stirred for 5 mins then partitioned between ethyl acetate and 2M HCl. Combined organic extracts were dried (MgSO4) and concentrated to give an oil which crystallised upon trituration with i-hexane. Filtration yielded the desired end product as an off-white powder (0.136 g, 67%); NMR δ (CD3SOCD3) 1.18 (t, 3H), 3.79 (s, 3H), 3.82 (d, 2H), 4.08 (q, 2H), 5.72 (s, 2H), 6.60-7.50 (in, 7H); M/z (+) 435 (M+), 133.

後処理

  1. customthen partitioned between ethyl acetate and 2M HCl
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customto give an oil which
  5. customcrystallised upon trituration with i-hexane
  6. filtrationFiltration

出典と根拠

ORDレコード
ord-b315c36a68e94c92b0bfc1166d03e9df
出典データセット
uspto-grants-2005_10
特許番号
US06953809B2

反応ノート

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