Acetic Acid → HCID 15950362, compound

HRID 641709Notes

Reaction equation

HRID 641709 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:30])[CH:12]2[CH2:29][N:16]3[C:17]4[C:22]([C:23]([CH2:24][C:25]([O:27]C)=[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.CO.[Li+].[OH-].CC(O)=O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:30])[CH:12]2[CH2:29][N:16]3[C:17]4[C:22]([C:23]([CH2:24][C:25]([OH:27])=[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 4

HCID 176Acetic AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 58399157HCID 58399157, compound

Product 1

HCID 15950362HCID 15950362, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 11 (0.38 g) in 10 mL of THF were added 5 mL of MeOH and 5 mL of 1N LiOH. After stirring for 2 h, 2 mL of AcOH was added and the mixture was partitioned between 50 mL of EtOAc and 20 mL of brine. The EtOAc extract was dried over Na2SO4 and filtered. The filtrate was concentrated and the residue was swished from 3:1 EtOAc/hexane to give 0.18 g of the title compound. 1H NMR (500 MHz, acetone-d6) δ 8.11 (m, 2H), 7.53 (d, 1H), 7.47 (t, 2H), 7.28 (d, 1H), 7.10 (dd, 1H), 7.04 (dd, 1H), 4.53 (m, 1H), 4.20 (m, 1H), 3.90 (t, 1H), 3.67 (d, 1H, A of AB), 3.60 (d, 1H, B of AB), 3.15 (m, 1H), 2.97 (3H), 2.85-2.92 (m, 1H), 1.90-2.00 (m, 1H), 1.70 (m, 1H).

Workup

  1. customthe mixture was partitioned between 50 mL of EtOAc and 20 mL of brine
  2. extractionThe EtOAc extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fab1713a990d40448725fe05d29fa3a5
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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