Pivalic acid → HCID 178456378, compound

HRID 1984032Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([O:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([NH:25][NH2:26])=[O:24])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:29](O)(=O)[C:30]([CH3:33])([CH3:32])[CH3:31].P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[C:30]([C:33]1[O:24][C:23]([C:22]2[CH:21]=[CH:20][C:19]([O:18][C@H:15]3[CH2:16][CH2:17][C@H:12]([C:10]([N:7]4[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]4)=[O:11])[CH2:13][CH2:14]3)=[CH:28][CH:27]=2)=[N:25][N:26]=1)([CH3:32])([CH3:31])[CH3:29]

Participants

Reactant 4

HCID 6417Pivalic acid

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 178456383HCID 178456383, compound

Product 1

HCID 178456378HCID 178456378, compoundYield 36.7%

Procedure

A mixture of 60 mg (0.15 mmol) of trans-4-[4-(4-Isopropyl-piperazine-1-carbonyl)-cyclohexyloxy]-benzoic acid hydrazide, 0.02 ml (0.2 mmol) of pivalic acid and 2 ml of phosphorus oxychloride was refluxed for 2 hr. To the mixture, 1N NaOH solution was added. The mixture was extracted with AcOEt, washed with saturated NaHCO3 solution, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1. The combined product fractions were evaporated to dryness to yield 25 mg (36%) of the title compound. MS (m/e): 455.4 (MH+).

Workup

temperaturewas refluxed for 2 hr
extractionThe mixture was extracted with AcOEt
washwashed with saturated NaHCO3 solution
dry with materialdried over Na2SO4
customevaporated
customThe residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1
customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record: ord-819aafcda43b4fe5b444f737279875ed
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544683B2

Reaction notes

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