Pivaloyl chloride → HCID 54435396, compound

HRID 234503Notes

Reaction equation

HRID 234503 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[C:13]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])([NH:21][C:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:23])[C:12]2=[O:36])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:37](Cl)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>N1C=CC=CC=1>[C:38]([C:37]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[C:13]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])([NH:21][C:22]([N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])=[O:23])[C:12]2=[O:36])(=[O:10])=[O:9])=[CH:4][CH:3]=1)=[O:42])([CH3:41])([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 19076557HCID 19076557, compound

Product 1

HCID 54435396HCID 54435396, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.400 g of the compound obtained in EXAMPLE 13 in 3 ml of pyridine is cooled to 0° C. and 0.100 g of pivaloyl chloride is added. The mixture is stirred for 18 hours, the temperature being allowed to rise to RT, and then evaporated under vacuum. The residue is extracted with AcOEt, washed with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether mixture. m=0.180 g. M.p.=228° C.

Workup

  1. customto rise to RT
  2. customevaporated under vacuum
  3. extractionThe residue is extracted with AcOEt
  4. washwashed with a 5% solution of potassium hydrogensulfate
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-77e79504f0534f128efbe1b0ea49a76f
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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