Sodium hydride → HCID 67953937, compound

HRID 2178557Notes

Reaction equation

HRID 2178557 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:19])=[C:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[N:10]=2)[CH:7]=1.[H-].[Na+].Cl[S:23]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:14]([O:13][C:12]([N:11]([C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]2[C:8]=1[CH3:19])[S:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=1)(=[O:25])=[O:24])=[O:18])([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 90090769HCID 90090769, compound

Product 1

HCID 67953937HCID 67953937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 6-C (0.70 g, 2.64 mmol) in DMF (20 mL) was cooled in an ice bath and treated with a 60% dispersion of NaH in mineral oil (0.126 g, 3.17 mmol) and stirred at ambient temp for 30 min. The solution was cooled on an ice bath and treated with methyl 4-(chlorosulfonyl)benzoate (1.24 g, added in portions). The resultant solution was stirred at ambient temperature for 18 hours. The solution was poured into ice water, and the resultant suspension was made basic with careful addition of a saturated aqueous solution of NaHCO3. The solid was collected by filtration, washed with water and air dried. The solid was pre-absorbed onto silica gel and purified by flash chromatography, using a gradient of EtOAc (10-60%) in heptanes as the eluant to afford compound 6-D as a colorless solid (1.1 g, 90%). MS: m/z 464.1 (MH+).

Workup

  1. temperatureThe solution was cooled on an ice bath
  2. filtrationThe solid was collected by filtration
  3. washwashed with water and air
  4. customdried
  5. customThe solid was pre-absorbed onto silica gel
  6. custompurified by flash chromatography
  7. customto afford compound 6-D as a colorless solid (1.1 g, 90%)

Sources & evidence

ORD record
ord-e989928ea98f4beeab1a92b80c58f035
Source dataset
uspto-grants-2015_06
Patent number
US09067935B2

Reaction notes

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