Dimethylformamide → HCID 53965189, compound

HRID 583197Notes

Reaction equation

HRID 583197 reaction equation
[H-].[Na+].FC(F)(F)[C:5]([NH:7][S:8]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=O.C[N:23]([CH3:26])[CH:24]=[O:25]>>[C:11]1([C@H:26]2[CH2:5][N:7]([S:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[NH:16][CH2:15][CH2:14]4)(=[O:10])=[O:9])[C:24](=[O:25])[NH:23]2)[CH:12]=[CH:13][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 21224875HCID 21224875, compound

Product 1

HCID 53965189HCID 53965189, compoundYield 68%

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% oily, 475 mg, 11.88 mmol) was suspended in 15 m of dimethylformamide and cooled down to 0° C. To the suspension was added N-trifluoroacetyl-indoline-5-sulfonamide (0.832 g, 2.97 mmol) prepared in Preparation 7 in several portions, and then the mixture was stirred at 0° C. for 10 min. Then, (S)-2-N-phenoxycarbonylamino-2-phenylethylmethane-sulfonate (1.0 g, 2.97 mmol) prepared in Preparation 6 was added thereto. The reaction mixture was stirred at 0° C. for 3 hours and further stirred at room temperature for 1 hour. After confirming the completion of reaction by TLC, the reaction mixture was poured into 30 m of ice. The resulting precipitate was collected and dried to afford 0.72 g of the title compound.

Workup

  1. customprepared in Preparation 7 in several portions
  2. additionwas added
  3. stirringThe reaction mixture was stirred at 0° C. for 3 hours
  4. stirringfurther stirred at room temperature for 1 hour
  5. customthe completion of reaction by TLC
  6. additionthe reaction mixture was poured into 30 m of ice
  7. customThe resulting precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-8359bf471d1b4733aa59b700729d4f89
Source dataset
uspto-grants-1999_07
Patent number
US05929103

Reaction notes

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