Aluminium lithium hydride → HCID 86588216, compound

HRID 1814315Notes

Reaction equation

HRID 1814315 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:49])[CH2:13][CH:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:34][CH3:35])=[S:33])=[CH:27][C:26]=1[O:36][CH2:37][CH2:38][C:39]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:40]=1[CH:41]=[CH:42][CH:43]=[N:44]2)(=[O:24])=[O:23])[C:15](N(OC)C)=[O:16])([CH3:10])([CH3:9])[CH3:8]>CCOCC.C1COCC1>[C:7]([O:11][C:12](=[O:49])[CH2:13][CH:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:34][CH3:35])=[S:33])=[CH:27][C:26]=1[O:36][CH2:37][CH2:38][C:39]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:40]=1[CH:41]=[CH:42][CH:43]=[N:44]2)(=[O:24])=[O:23])[CH:15]=[O:16])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86588217HCID 86588217, compound

Product 1

HCID 86588216HCID 86588216, compoundYield 505.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

A mixture of 2 mL THF and 0.8 mL 1M LiAlH4 solution in ether was cooled to −65° C. in a chloroform/dry ice bath. A mixture if 0.18 g (0.29 mmol) N-methoxy-N-methyl--3-[4-(3-methyl-thioureido)-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-succinamic acid tert-butyl ester in 3 mL THF was added dropwise and the reaction mixture was stirred 30 min at −65° C. TLC analysis showed starting material consumed. The reaction was quenched cold with 1 mL 1M aqueous potassium sodium tartrate solution and allowed to reach room temperature. The product was partioned between 75 mL brine and 50 mL EtOAc. The product was extracted with 50 EtOAc, the combined organic extracts dried over anhydrous magnesium sulfate, filtered, concentrated and purified on silica with 1:1 EtOAc:hexanes to give 0.84 g (52%) of 3-[4-(3-methyl-thioureido)-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester as a colorless glass. MS (APCI) m/z 573 (M+1).

Workup

  1. customconsumed
  2. customThe reaction was quenched cold with 1 mL 1M aqueous potassium sodium tartrate solution
  3. customto reach room temperature
  4. extractionThe product was extracted with 50 EtOAc
  5. dry with materialthe combined organic extracts dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on silica with 1:1 EtOAc

Sources & evidence

ORD record
ord-8cb23d51eda54ebeaa7a41e9796622a9
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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