Thioglycolic Acid → HCID 58417061, compound

HRID 1805289Notes

Reaction equation

HRID 1805289 reaction equation
[N+](C1C=CC(S([N:13]([C@H:20]2[CH2:24][CH2:23][N:22]([C:25]3[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=3)[CH2:21]2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)(=O)=O)=CC=1)([O-])=O.[OH-].[Li+].C(O)(=O)CS>CN(C=O)C>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C@H:20]1[CH2:24][CH2:23][N:22]([C:25]2[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[CH:27][CH:26]=2)[CH2:21]1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 3939Lithium HydroxideHCID 86623233HCID 86623233, compound

Product 1

HCID 58417061HCID 58417061, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 12 (1.41 g, 2.68 mmol) in DMF (13 mL), were successively added lithium hydroxide (382 mg, 9.09 mmol) and thioglycolic acid (274 μL, 3.94 mmol). The mixture was stirred for 18 h at r.t., the solvent was removed in vacuo at 80° C. and the residue was partitioned between EtOAc and H2O. The organic layer was collected, washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc/Hexanes (40:60) as an eluent, to afford the title compound 13 (511 mg, 47% yield) as a light yellow oil. 1H NMR: (DMSO-d6) d(ppm): 7.98 (dd, J=5.5, 1.6 Hz, 1H), 7.68 (d, J=8.8 Hz, 2H), 7.35 (td, J=7.0, 2.0 Hz, 1H), 6.80 (d, J=6.3 Hz, 1H), 6.52 (d, J=9.0 Hz, 2H), 6.49-6.46 (m, 2H), 4.52-4.49 (m, 1H), 3.64 (dd, J=10.5, 6.5 Hz, 1H), 3.48-3.44 (m, 1H), 3.39-3.33 (m, 1H), 3.16 (dd, J=10.0, 4.5 Hz, 1H), 2.30-2.24 (m, 1H), 2.00-2.19 (m, 1H), 1.48 (s, 9H). LRMS (ESI): (calc.) 339.19 (found) 340.1 (MH)+

Workup

  1. customthe solvent was removed in vacuo at 80° C.
  2. customthe residue was partitioned between EtOAc and H2O
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-df583f2eb7614cd0a0e9185495d6be74
Source dataset
uspto-grants-2013_01
Patent number
US08354445B2

Reaction notes

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