Pivaloyl chloride → HCID 54435396, compound

HRID 965551Notes

Reaction equation

HRID 965551 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-ac3206e525544889ba0961844106e1e8
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

Loading…