Thioglycolic Acid → HCID 59737563, compound

HRID 1907737Notes

Reaction equation

HRID 1907737 reaction equation
[N+](C1C=CC(S([N:13]([C@H:20]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[CH:53]=[CH:52][C:29]([C:30]([NH:32][C:33]4[CH:38]=[C:37]([C:39]5[S:40][CH:41]=[CH:42][CH:43]=5)[CH:36]=[CH:35][C:34]=4[NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:31])=[CH:28][CH:27]=3)[CH2:21]2)[C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=O)=O)=CC=1)([O-])=O.SCC(O)=O.[OH-].[Li+].CCOC(C)=O>CN(C=O)C.CO>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([NH:13][C@H:20]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([NH:32][C:33]4[CH:38]=[C:37]([C:39]5[S:40][CH:41]=[CH:42][CH:43]=5)[CH:36]=[CH:35][C:34]=4[NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:48])[CH3:49])=[O:31])=[CH:52][CH:53]=3)[CH2:21]2)[CH:15]=1

Participants

7

Reactant 4

HCID 1133Thioglycolic AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59737515HCID 59737515, compound

Product 1

HCID 59737563HCID 59737563, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 247 (0.65 g, 0.86 mmol) in DMF (5 mL) was added mercaptoacetic acid (0.103 g, 1.12 mmol) followed by solid lithium hydroxide (0.108 g, 2.58 mmol). The reaction mixture was allowed to stir at room temperature for 18 h and then at 70° C. for 4 h. The reaction mixture was concentrated, diluted with AcOEt and extracted with H2O, saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated to give a yellow oil which was purified by flash chromatography (eluents: 100% EtOAc then 2.5% MeOH/1% Et3N/96.5% EtOAc and finally, 5% MeOH/1% Et3N/94% EtOAc) to provide title compound 248 (0.333 g, 68% yield).

Workup

  1. waitat 70° C. for 4 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with AcOEt
  4. extractionextracted with H2O, saturated NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil which
  9. customwas purified by flash chromatography (eluents

Sources & evidence

ORD record
ord-d42de482b728451c9591e83346a5f9f3
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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