Acetic Acid → HCID 58940638, compound

HRID 548940Notes

Reaction equation

HRID 548940 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([NH:12][C@@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[N:9]=[CH:8][N:7]=1.C=O.[C:22](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([NH:12][C@@H:13]2[CH2:17][CH2:16][N:15]([CH3:22])[CH2:14]2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57394626HCID 57394626, compound

Product 1

HCID 58940638HCID 58940638, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the compound of example 7 (38 mg, 0.144 mmol) in THF (1.5 mL) containing aqueous formaldehyde (11 μL, 0.144 mmol, 37% in water) and acetic acid (8.3 μL, 0.144 mmol) was treated with sodium triacetoxyborohydride (37 mg, 0.173 mmol) and stirred at ambient temperature for 10 min. The reaction mixture was applied directly to SCX resin, eluting non-basic compounds with MeOH and the basic compounds with 1 N ammonia in MeOH. The basic washings were concentrated in vacuo and purified by flash column chromatography on silica gel eluting with DCM:MeOH:0.880 ammonia (1:0:0 changing to 40:10:1, by volume) further purification on reverse phase silica eluting with water:acetonitrile (1:0 changing to 19:1 by volume) gave the title compound as a white solid (14 mg, 35%).

Workup

  1. washeluting non-basic compounds with MeOH
  2. concentrationThe basic washings were concentrated in vacuo
  3. custompurified by flash column chromatography on silica gel eluting with DCM
  4. customMeOH:0.880 ammonia (1:0:0 changing to 40:10:1, by volume) further purification on reverse phase silica eluting with water:acetonitrile (1:0 changing to 19:1 by volume)

Sources & evidence

ORD record
ord-ece266e447824b7ea891d35fa4653c6b
Source dataset
uspto-grants-2011_05
Patent number
US07943628B2

Reaction notes

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