Formaldehyde → HCID 54526089, compound

HRID 1249876Notes

Reaction equation

HRID 1249876 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:23])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18](N)[CH:17]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:25]([BH3-])#[N:26].[Na+].C=O.O1CCC[CH:32]1CO.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:23])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:26]([CH3:25])[CH3:32])[CH:17]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 7360Tetrahydrofurfuryl alcoholHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 54049431HCID 54049431, compound

Product 1

HCID 54526089HCID 54526089, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

A solution of [4-(3-amino-benzoylamino)-phenyl]-carbamic acid t-butyl ester (505 mg), sodium cyanoborohydride (250 mg), acetic acid (3 drops) and 40% aqueous formaldehyde (4 mL) in 1:2 tetrahydrofuran-methanol (15 mL) is stirred for 15 minutes, and then poured into saturated aqueous sodium bicarbonate and extracted into ethyl acetate. The ethyl acetate solution is dried over anhydrous potassium carbonate and concentrated under reduced pressure to give a solid which is recrystallized from acetonitrile to provide a pale pink crystalline solid.

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe ethyl acetate solution is dried over anhydrous potassium carbonate
  3. concentrationconcentrated under reduced pressure
  4. customto give a solid which
  5. customis recrystallized from acetonitrile
  6. customto provide a pale pink crystalline solid

Sources & evidence

ORD record
ord-75d8977129fd461ea3fec93ad458fd15
Source dataset
uspto-grants-2002_01
Patent number
US06335350B1

Reaction notes

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