Dimethylformamide → HCID 86601495, compound

HRID 270135Notes

Reaction equation

HRID 270135 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[C:14]([OH:16])[C:13]([NH:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:11]=1[Cl:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=C(S(O[CH2:40][C@:41]2(C)[CH2:43][O:42]2)(=O)=O)C=CC=1)([O-])=O.CN(C=O)C>O>[C:1]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:40][C@@H:41]2[CH2:43][O:42]2)[C:13]([NH:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][C:11]=1[Cl:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68962473HCID 68962473, compoundHCID 86597620HCID 86597620, compound

Product 1

HCID 86601495HCID 86601495, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4-(benzoylamino)-2-chloro-5-hydroxyphenyl benzoate (103 mg, 0.28 mmol) and [(2S)-2-methyloxiran-2-yl]methyl 3-nitrobenzenesulfonate (73 mg, 0.28 mmol) in DMF (3 mL) cesium carbonate (98 mg, 0.3 mmol) was added. The stirring was continued at ambient temperature over night. The mixture was poured into water and partitioned between water and ethylacetate. The organic phase was washed with water, dried and concentrated in vacuo to give a white solid (117 mg, 98%). The solid was used without further purification.

Workup

  1. waitThe stirring was continued at ambient temperature over night
  2. custompartitioned between water and ethylacetate
  3. washThe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6847922d62a4c0e91d7290105971046
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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