Potassium Sodium Tartrate → 3-[4-Acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester

HRID 1814301Notes

Reaction equation

HRID 1814301 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:48])[CH2:13][CH:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][C:26]=1[O:35][CH2:36][CH2:37][C:38]1[CH:47]=[CH:46][CH:45]=[C:44]2[C:39]=1[CH:40]=[CH:41][CH:42]=[N:43]2)(=[O:24])=[O:23])[C:15](N(OC)C)=[O:16])([CH3:10])([CH3:9])[CH3:8].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC.C1COCC1>[C:7]([O:11][C:12](=[O:48])[CH2:13][CH:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][C:26]=1[O:35][CH2:36][CH2:37][C:38]1[CH:47]=[CH:46][CH:45]=[C:44]2[C:39]=1[CH:40]=[CH:41][CH:42]=[N:43]2)(=[O:24])=[O:23])[CH:15]=[O:16])([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydride2×HCID 865882063-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 865882073-[4-Acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Lithium aluminum hydride solution (0.9 mL of a 1.0 M solution in ether) was dissolved in 15 mL diethyl ether and cooled to 65° C. 3-[4-Acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester (180 mg, 0.3 mmol) was dissolved in 5 mL THF and added to the LiAlH4 solution via canula. The reaction was stirred for 10 minutes at 65° C. and then warmed to −44° C. for 15 minutes. The reaction was cooled to −65° C. and saturated Rochelle's salt was added. The reaction was warmed to room temperature, and then extracted with ethyl acetate. The extract was dried with sodium sulfate, and then concentrated in vacuo. The crude product was chromatographed with 5% methanol in ethyl acetate to yield 3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester 130 mg (80%) of a light brown solid.

Workup

  1. temperaturewarmed to −44° C. for 15 minutes
  2. temperatureThe reaction was cooled to −65° C.
  3. temperatureThe reaction was warmed to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-befec5477a814b1a924a79bc10ed5002
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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