Formaldehyde → HCID 58542388, compound

HRID 1951897Notes

Reaction equation

HRID 1951897 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[N:29]3[C:25]([S:26][C:27]([C:33]([N:35]4[CH2:49][C@H:48]([F:50])[CH2:47][C@H:36]4[C:37]([N:39]4[CH2:46][C:43]5([CH2:45][CH2:44]5)[NH:42][CH2:41][CH2:40]4)=[O:38])=[O:34])=[C:28]3[CH:30]([CH3:32])[CH3:31])=[N:24][C@:23]2([C:52]2[CH:53]=[N:54][C:55]([Cl:58])=[CH:56][CH:57]=2)[CH3:51])=[CH:18][C:17]=1[F:59].C=O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[N:29]3[C:25]([S:26][C:27]([C:33]([N:35]4[CH2:49][C@H:48]([F:50])[CH2:47][C@H:36]4[C:37]([N:39]4[CH2:46][C:43]5([CH2:44][CH2:45]5)[N:42]([CH3:1])[CH2:41][CH2:40]4)=[O:38])=[O:34])=[C:28]3[CH:30]([CH3:31])[CH3:32])=[N:24][C@:23]2([C:52]2[CH:53]=[N:54][C:55]([Cl:58])=[CH:56][CH:57]=2)[CH3:51])=[CH:18][C:17]=1[F:59]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58542358HCID 58542358, compound

Product 1

HCID 58542388HCID 58542388, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium triacetoxyborohydride (267 mg, 1.26 mmol) was added to a 1,4-dioxane (10 ml) solution of the compound (340 mg, 0.503 mmol) obtained in Step 2 of Example 1 and 37% aqueous paraformaldehyde solution (0.41 ml, 5.05 mmol) at room temperature and the resulting mixture was stirred for 17 hours. Saturated aqueous sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography [chloroform:methanol=50:1 (v/v)) to give the title compound (309 mg, 89%) as a colorless solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel chromatography [chloroform

Sources & evidence

ORD record
ord-8a59d1f643fb4a3ea6eed05bf82baa78
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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