Thiophenol → HCID 70015288, compound

HRID 1370736Notes

Reaction equation

HRID 1370736 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([NH:11][C@H:12]([C:24]([OH:26])=[O:25])[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)(=[O:16])=[O:15])(=[O:10])[CH3:9].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:8]([NH:11][C@H:12]([C:24]([OH:26])=[O:25])[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 70016103HCID 70016103, compound

Product 1

HCID 70015288HCID 70015288, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
9 °C

Procedure

Thiophenol (7.27 g, 71.0 mmol) was added to a solution of the title compound of Example 11b (17.0g, 59.0 mmol) and K2CO3 (24.4 g, 177 mmol) in DMF (200 mL). After heating at 9 degrees C. for 2 hours, the mixture was concentrated under a stream of N2. The solution was acidified to pH=1 with 1M KHSO4, extracted into EtOAc (2×) and the organic phases were washed with brine and dried over MgSO4. The solution was concentrated in vacuo to yield the title compound as a white solid and was carried on without additional purification.

Workup

  1. concentrationthe mixture was concentrated under a stream of N2
  2. extractionextracted into EtOAc (2×)
  3. washthe organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-327a4cb73b614270ab30ec0a29c8cd98
Source dataset
uspto-grants-2003_06
Patent number
US06583299B1

Reaction notes

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