Aluminium lithium hydride → (S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester

HRID 1814282Notes

Reaction equation

HRID 1814282 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:44])[CH2:13][C@H:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH2:32][CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[N:36][CH:35]=1)(=[O:24])=[O:23])[C:15](N(OC)C)=[O:16])([CH3:10])([CH3:9])[CH3:8].C1COCC1.C(OCC)C>C(OCC)C>[C:7]([O:11][C:12](=[O:44])[CH2:13][C@H:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH2:32][CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[N:36][CH:35]=1)(=[O:24])=[O:23])[CH:15]=[O:16])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21868444Ether tetrahydrofuranHCID 86588200(S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 86588201(S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To lithium aluminum hydride (0.45 mL of 1.0 M solution in diethyl ether) in diethyl ether (7 mL) at −65° C. was added (S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester in 1:1 THF/diethylether (4 mL). After 1 hour, the reaction was quenched by addition of 1.0N sodium hydroxide (2 mL) and the reaction was warmed to room temperature. The organic layer was separated and evaporated. The resulting residue was chromatographed on silica gel eluting with 10% diethyl ether in ethyl acetate to give (S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester as a colorless foam (39 mg). MS (APCI) m/z 485.1 (M+1).

Workup

  1. customthe reaction was quenched by addition of 1.0N sodium hydroxide (2 mL)
  2. customThe organic layer was separated
  3. customevaporated
  4. customThe resulting residue was chromatographed on silica gel eluting with 10% diethyl ether in ethyl acetate

Sources & evidence

ORD record
ord-8674c564ba9c4c7da2b94115845136ce
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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