Formaldehyde → HCID 19076422, compound

HRID 234537Notes

Reaction equation

HRID 234537 reaction equation
C=O.[C:3]([BH3-])#[N:4].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:12](=[O:34])[C:11]2([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[Cl:50])[NH:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42]N[CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+]>CO.CC(O)=O.Cl.O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([S:17]([C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28])=[CH:24][CH:25]=1)(=[O:18])=[O:19])[C:12](=[O:34])[C:11]2([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[Cl:50])[NH:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][N:4]([CH3:3])[CH2:40][CH2:39]1

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 19076410HCID 19076410, compound

Product 1

HCID 19076422HCID 19076422, compoundYield 60.6%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.03 g of paraformaldehyde and 0.02 g of sodium cyanoborohydride are added in portions in 4 hours to a solution of 0.16 g of the compound obtained in EXAMPLE 201 in 4 ml of MeOH and 1 ml of AcOH. The mixture is stirred overnight at RT, 5 drops of concentrated HCl are added, water is then added after 10 minutes and the reaction mixture is rendered alkaline by the addition of potassium carbonate. The organic solvents are concentrated under vacuum, the residue is extracted with DCM and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/MeOH mixture (88/12; v/v) as the eluent to give 0.099 g of the expected product after crystallization from a DCM/hexane/iso ether mixture.

Workup

  1. concentrationThe organic solvents are concentrated under vacuum
  2. extractionthe residue is extracted with DCM
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica using a DCM/MeOH mixture (88/12; v/v) as the eluent

Sources & evidence

ORD record
ord-a4bb8ffbb2214adfa310517e9ee7610c
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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