Hydrochloric Acid → HCID 15379729, compound

HRID 1368170Notes

Reaction equation

HRID 1368170 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([N:10]2[CH:19]([C:20]([OH:22])=O)[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.CN1CCOCC1.ClC(OCC(C)C)=O.C[Si](C)(C)[O:40][NH2:41].Cl>C1COCC1.O>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([N:10]2[CH:19]([C:20]([NH:41][OH:40])=[O:22])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 14989999HCID 14989999, compound

Product 1

HCID 15379729HCID 15379729, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.3 g (7.5 mmol) of the carboxylic acid 26b are dissolved in 40 ml of absolute THF and, at −20° C., admixed successively with 1.2 g (12 mmol) of N-methylmorpholine and 1.1 g (7.5 mmol) of isobutyl chloroformate. After 30 min, the mixture is admixed with 3.9 g (37.5 mmol) of O-trimethylsilylhydroxylamine and stirred at RT for a further 5 h. 200 ml of water are added and the mixture is acidified with dilute HCl and extracted repeatedly with dichloromethane. The pooled organic phases are dried over Na2SO4 and concentrated under reduced pressure. The resulting oil is chromatographed under pressure over silica gel 60 using ethyl acetate/dichloromethane (1:1) as mobile phase. Recrystallization of the product fractions from ethyl acetate gave crystalline hydroxamic acid 26c. Yield: 1.4 9 (55% of theory) Melting point: 164-165° C. (decomposition).

Workup

  1. extractionextracted repeatedly with dichloromethane
  2. dry with materialThe pooled organic phases are dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting oil is chromatographed under pressure over silica gel 60 using ethyl acetate/dichloromethane (1:1) as mobile phase
  5. customRecrystallization of the product fractions from ethyl acetate

Sources & evidence

ORD record
ord-7a4abcb8eb7e424193ce4e290970e152
Source dataset
uspto-grants-2003_06
Patent number
US06573277B2

Reaction notes

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