Acetic Acid → HCID 86687134, compound

HRID 1402291Notes

Reaction equation

HRID 1402291 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C@H:11]3[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]3)=[N:9][N:10]=2)[CH:7]=1.C=O.[CH3:19]C(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C@H:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH3:19])[CH2:12]3)=[N:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86687132HCID 86687132, compound

Product 1

HCID 86687134HCID 86687134, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a yellow solution of Intermediate 88c (220 mg, 1.00 mmol), formaldehyde (37% in water, 0.811 mL, 10.0 mmol) and AcOH (0.057 mL, 1.00 mmol) in DCM-MeOH (5:1, 12 mL) was added NaBH(OAc)3 (424 mg, 2.00 mmol) (CARE: gas evolution) and the solution stirred at RT for 2 h. The solution was concentrated in vacuo to 5 mL volume, then applied to an SCX-2 cartridge (10 g) and washed with MeOH (50 mL). The product was eluted with 2M NH3 in MeOH (50 mL); concentration in vacuo gave the title compound as a pale yellow gum, that became a white solid on standing (234 mg, quant.). LCMS (Method 3): Rt 0.45 min, m/z 235 [MH+].

Workup

  1. concentrationThe solution was concentrated in vacuo to 5 mL volume
  2. washwashed with MeOH (50 mL)
  3. washThe product was eluted with 2M NH3 in MeOH (50 mL)
  4. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-6953835b0023480aa68af4f80f79294e
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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