Formaldehyde → HCID 11421768, compound

HRID 2267119Notes

Reaction equation

HRID 2267119 reaction equation
OC1C=CC(C[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:39])[NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:20][CH2:19]2)=[O:15])=CC=1.[CH2:42]=[O:43].C([BH3-])#N.[Na+].CO>[Cl-].[Zn+2].[Cl-]>[OH:43][C:42]1[CH:30]=[CH:29][C:28]([CH2:33][CH2:34][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:39])[NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:20][CH2:19]2)=[O:15])=[CH:27][CH:32]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 11455752HCID 11455752, compound

Product 1

HCID 11421768HCID 11421768, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a solution of the product of Example 2 (300 mg, 0.38 mmol) in 4 mL of MeOH was added zinc chloride (26 mg, 0.19 mmol, 0.5 eq), followed by formaldehyde (37% aqueous solution, 141 μL, 1.9 mmol, 10 eq). The solution was stirred at room temperature for 30 minutes and then sodium cyanoborohydride (24 mg, 0.38 mmol, 1 eq) was added. The reaction mixture was stirred at room temperature for 2 hours. and then the solvent was removed in vacuo. The crude product was purified by reverse phase HPLC to afford the title compound as a bis(trifluoroacetate) salt. MS m/z [M+H+] calc'd for C34H44N4O4 573.3; found 573.3.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. customand then the solvent was removed in vacuo
  3. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-aff560108ee84dddaf6785bf62d27632
Source dataset
uspto-grants-2010_12
Patent number
US07858792B2

Reaction notes

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