Formaldehyde → HCID 68450887, compound

HRID 2104440Notes

Reaction equation

HRID 2104440 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[NH:21][C:22]([C:24]1[S:32][C:31]3[CH2:30][CH2:29][NH:28][CH2:27][C:26]=3[CH:25]=1)=[O:23])=[O:13])=[CH:6]2.C=O.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.Cl.O.C(O)(=O)C.C(N(CC)CC)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[NH:21][C:22]([C:24]1[S:32][C:31]3[CH2:30][CH2:29][N:28]([CH3:35])[CH2:27][C:26]=3[CH:25]=1)=[O:23])=[O:13])=[CH:6]2

Participants

10

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 68451900HCID 68451900, compound

Product 1

HCID 68450887HCID 68450887, compoundYield 96.7%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The compound (171 mg) obtained in Example 17 was suspended in methylene chloride (10 mL), and triethylamine (0.104 mL) was added, followed by stirring at room temperature for 10 minutes. After acetic acid (0.059 mL) was added to the reaction mixture, a 35% formalin (0.070 mL) and sodium triacetoxyborohydride (118 mg) were added, and the mixture was stirred at room temperature for 30 minutes. After 1N aqueous sodium hydroxide (3 mL) was added to the reaction mixture, water was added for partitioning the mixture. After the resultant organic layer was dried over sodium sulfate anhydrate, the solvent was then distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=50:3) to give a colorless foamy substance. This substance was suspended in 1N hydrochloric acid, and the suspension was concentrated under reduced pressure to give the title compound (85 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. additionwas added
  3. customfor partitioning the mixture
  4. dry with materialAfter the resultant organic layer was dried over sodium sulfate anhydrate
  5. distillationthe solvent was then distilled away under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=50:3)
  7. customto give a colorless foamy substance
  8. concentrationthe suspension was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5eaa720e28594b56a93b91d82c94ff04
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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