Acetic Acid → HCID 69620851, compound

HRID 1628271Notes

Reaction equation

HRID 1628271 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C([O-])(O)=O.[Na+].CC(O)=O.[S:24]1[CH:28]=[C:27]([CH:29]=O)[N:26]=[CH:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:8]1([CH2:7][C@H:5]([NH:6][CH2:29][C:27]2[N:26]=[CH:25][S:24][CH:28]=2)[C:4]([O:3][CH3:2])=[O:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 516892Sodium BicarbonateHCID 2763214Thiazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69620851HCID 69620851, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-Phenylalanine methyl ester HCl 34.8.A (2.15 g, 10.0 mmol) was partitioned with DCM and saturated NaHCO3. The aqueous layer was extracted with DCM (2×). The organic layers were combined, dried with sodium sulfate, filtered, and concentrated. The residue was dissolved in DCM (30 ml) and AcOH (571 μL, 10 mmol), thiazole-4-carboxaldehyde 34.8.B (1.13 g, 10 mmol), and NaBH(OAc)3 (4.24 g, 20 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with NaHCO3(sat) and extracted with DCM. The organic extracts were dried with sodium sulfate, filtered, and concentrated. The resulting residue was partially purified on a silica gel column (120 g, 0-8% MeOH:DCM) to yield 34.8.0 as a crude oil (2.25 g).

Workup

  1. extractionThe aqueous layer was extracted with DCM (2×)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in DCM (30 ml)
  6. customThe reaction mixture was quenched with NaHCO3(sat)
  7. extractionextracted with DCM
  8. dry with materialThe organic extracts were dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue was partially purified on a silica gel column (120 g, 0-8% MeOH:DCM)

Sources & evidence

ORD record
ord-cc558c730aab44e89513c4c293f3f7ea
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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