Thioglycolic Acid → HCID 86679547, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][S:13]([CH3:16])(=[O:15])=[O:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[SH:48][CH2:49][C:50]([OH:52])=[O:51]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([S:48][CH2:49][C:50]([OH:52])=[O:51])=[O:9])=[CH:5][C:4]=1[O:12][S:13]([CH3:16])(=[O:15])=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 4-methoxy-3-(methylsulfonyloxy)benzoic acid (prepared in an analogous manner to that described in Scheme 23, Step 2 and 3) (0.362 g, 1.470 mmol) in dry DMF (10.7 ml), HATU (0.559 g, 1.470 mmol) and N-methylmorpholine (0.162 ml, 1.470 mmol) were added. The resulting mixture was stirred at 50° C. under nitrogen until complete conversion of the starting acid into the activated specie (detected by UPLC-MS). Then the solution was allowed to warm to RT and 2-mercaptoacetic acid (0.102 ml, 1.470 mmol) was added drop wise; the resulting mixture was stirred overnight at RT. The solvent was removed under vacuum and the residue was partitioned between EtOAc and HCl 1N; the organic phase was dried over Na2SO4 and the solvent was removed. The crude was purified by preparative HPLC to afford 2-(4-methoxy-3-(methylsulfonyloxy)-benzoylthio)acetic acid (0.152 g, 0.474 mmol, 32.3% yield, MS/ESI+ 342.9 [MNa]+).
Workup
- temperatureto warm to RT
- stirringthe resulting mixture was stirred overnight at RT
- customThe solvent was removed under vacuum
- customthe residue was partitioned between EtOAc and HCl 1N
- dry with materialthe organic phase was dried over Na2SO4
- customthe solvent was removed
- customThe crude was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-4930a31f99df477fb026a7ac9aabe008
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09265768B2
Reaction notes
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