Acetic Acid → HCID 58399157, compound

HRID 641708Notes

Reaction equation

HRID 641708 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:31])[CH:12]2[CH2:30][N:16]3[C:17]4[C:22]([C:23]([C:24](=O)[C:25]([O:27][CH3:28])=[O:26])=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+].CC(O)=O>CO.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:31])[CH:12]2[CH2:30][N:16]3[C:17]4[C:22]([C:23]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 58399162HCID 58399162, compound

Product 1

HCID 58399157HCID 58399157, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.8 g of the product of Step 10 in 100 mL of MeOH and 20 mL of THF was added 0.3 g of NaBH4. After stirring for 1 h at room temperature, 2 mL of AcOH was added and the reaction mixture was concentrated and the residue was portioned between 50 mL of brine and 150 mL of EtOAc. The organic layer was separated and dried over Na2SO4. After filtration, the filtrate was concentrated and the residue was dissolved in 5 mL of CH2Cl2, and treated with 5 mL of Et3SiH and 3 mL of TFA. After stirring for 30 min at room temperature, the reaction mixture was concentrated and the residue was purified by Combiflash eluted with a gradient up to 70% EtOAc/hexane to give 0.3 g of the title compound. 1H NMR (500 MHz, acetone-d6) δ 8.10 (m, 2H), 7.45-7.52 (m, 3H), 7.27 (d, 1H), 7.10 (m, 1H), 7.01 (m, 1H), 4.53 (m, 1H), 4.18 (m, 1H), 3.88 (t, 1H), 3.60 (s, 3H), 3.13 (m, 1H), 2.97 (s, 3H), 2.86 (m, 1H), 1.90-2.00 (m, 1H), 1.70 (m, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. dissolutionthe residue was dissolved in 5 mL of CH2Cl2
  7. additiontreated with 5 mL of Et3SiH and 3 mL of TFA
  8. stirringAfter stirring for 30 min at room temperature
  9. concentrationthe reaction mixture was concentrated
  10. customthe residue was purified by Combiflash
  11. washeluted with a gradient up to 70% EtOAc/hexane

Sources & evidence

ORD record
ord-416d5f83d4994a3eab6f1a8330165235
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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