Acetic Acid → HCID 22310861, 화합물

HRID 967105노트

반응식

HRID 967105 반응식
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]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydrideHCID 22310882HCID 22310882, 화합물

생성물 1

HCID 22310861HCID 22310861, 화합물수율 67%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b315c36a68e94c92b0bfc1166d03e9df
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953809B2

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