Formaldehyde → HCID 86595610, compound

HRID 2117943Notes

Reaction equation

HRID 2117943 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[N:17]=[C:18]([NH:30][C:31](=[O:33])[CH3:32])[S:19][C:20]=2[CH2:21][NH:22][CH2:23][CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C=O.[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.O.CO>[C:31]([NH:30][C:18]1[S:19][C:20]([CH2:21][N:22]([CH2:23][CH2:24][C:25]([N:27]([CH3:28])[CH3:29])=[O:26])[CH3:37])=[C:16]([CH2:15][CH2:14][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:6](=[O:34])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:13][CH:12]=2)[N:17]=1)(=[O:33])[CH3:32]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 86595611HCID 86595611, compound

Product 1

HCID 86595610HCID 86595610, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Step 1 (100 mg) in dichloromethane (1.5 mL) was added formaline (35%, 87.6 μl). To this suspension was added 0.05 ml of MeOH. Then, sodium triacetoxyborohydride (433 mg) was added, and the mixture was stirred for 12 hrs. To the mixture were added water and 1N NaOH to adjust pH of aquaous phase (ca. pH 8-9). The mixture was extracted with dichloromethane. The organic layer was dried with MgSO4 and concentrated under redused pressure. Resulting oil was purified by silica gel column chromatograph (mixed solvent of CH2Cl2/MeOH 15/1 as an eluent) to give tert-butyl {4-[2-(2-(acetylamino)-5-{[[3-(N,N-dimethylamino)-3-oxopropyl](methyl)amino]methyl}-1,3-thiazol-4-yl)ethyl]phenyl}carbamate as pale yellow oil (90.4 mg).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated under redused pressure
  4. customResulting oil
  5. customwas purified by silica gel column chromatograph (
  6. additionmixed solvent of CH2Cl2/MeOH 15/1 as an eluent)

Sources & evidence

ORD record
ord-991b79769fe04121a455261d09de0070
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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