Formaldehyde → HCID 76903421, compound

HRID 1478828Notes

Reaction equation

HRID 1478828 reaction equation
[B:1]([C@@H:4]([NH:16][C:17]([C:19]1[C:27]2[CH2:26][CH2:25][NH:24][CH2:23][C:22]=2[S:21][CH:20]=1)=[O:18])[CH2:5][C:6]1[C:7](O)=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])([OH:3])[OH:2].[CH2:28]=O>CO.[Pd]>[OH:2][B:1]1[C@@H:4]([NH:16][C:17]([C:19]2[C:27]3[CH2:26][CH2:25][N:24]([CH3:28])[CH2:23][C:22]=3[S:21][CH:20]=2)=[O:18])[CH2:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]=2[O:3]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 86725239HCID 86725239, compound

Product 1

HCID 76903421HCID 76903421, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To (R)-3-(2-borono-2-(4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamido)ethyl)-2-hydroxybenzoic acid (10.0 mg from Example 4) in MeOH (5 mL) was added formaldehyde (1.0 mL, 37% solution), followed by 10% Pd/C (20 mg). The reaction mixture was hydrogenated under H2 balloon for 3 hr. The reaction mixture was filtrated and the solvent was removed under vacuum. The final product was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 387 (MH)+.

Workup

  1. customfor 3 hr
  2. filtrationThe reaction mixture was filtrated
  3. customthe solvent was removed under vacuum
  4. customThe final product was purified by reverse phase preparative HPLC
  5. customdried

Sources & evidence

ORD record
ord-be301492b9594d98942fc2c3caaeca24
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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