Acetic Acid → HCID 22310861, compound

HRID 967105Notes

Reaction equation

HRID 967105 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 22310861HCID 22310861, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b315c36a68e94c92b0bfc1166d03e9df
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

Loading…