Formaldehyde → HCID 68973728, compound

HRID 657575Notes

Reaction equation

HRID 657575 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:34]([O:35][CH3:36])=[CH:33][C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:32])[CH2:14][CH2:15][NH:16][CH2:17][CH:18]3[CH2:25][C:24]4[C:19]3=[CH:20][CH:21]=[C:22]([O:26][CH2:27][C:28]([NH:30][CH3:31])=[O:29])[CH:23]=4)[CH2:11][CH2:12][C:6]=2[CH:5]=1.C=O.[C:39]([BH3-])#N.[Na+]>C(#N)C>[ClH:1].[CH3:36][O:35][C:34]1[C:4]([O:3][CH3:2])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([C:13](=[O:32])[CH2:14][CH2:15][N:16]([CH2:17][CH:18]3[CH2:25][C:24]4[C:19]3=[CH:20][CH:21]=[C:22]([O:26][CH2:27][C:28]([NH:30][CH3:31])=[O:29])[CH:23]=4)[CH3:39])[CH2:9][CH2:8][C:7]=2[CH:33]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68971896HCID 68971896, compound

Product 1

HCID 68973728HCID 68973728, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At ambient temperature, to 0.83 g (1.72 mmol) of the compound obtained in Step C of Example 84, dissolved in 32 mL of acetonitrile, there are added, all at once, 1.4 mL (17.2 mmol) of 37% aqueous formaldehyde solution and then 0.22 g (3.44 mmol) of sodium cyanoborohydride. After stirring for 45 minutes at ambient temperature, concentration is carried out and the residue is taken up in 30 mL of water; the aqueous phase is extracted twice with 30 mL of dichloromethane; the organic phases are combined, washed with 30 mL of water and dried over magnesium sulphate. After concentration, the residue is chromatographed over silica (eluant: dichloromethane/ethanol/ammonia 95/5/0.5) to yield the desired compound in the form of the base.

Workup

  1. additionthere are added
  2. concentrationconcentration
  3. extractionthe aqueous phase is extracted twice with 30 mL of dichloromethane
  4. washwashed with 30 mL of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationAfter concentration
  7. customthe residue is chromatographed over silica (eluant: dichloromethane/ethanol/ammonia 95/5/0.5)

Sources & evidence

ORD record
ord-cecdc60b877844b388882fc4b8e06adc
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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