Aluminium lithium hydride → (S)-3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester

HRID 1814333Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:47])[CH2:13][CH:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][C:26]=1[O:34][CH2:35][CH2:36][C:37]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH:39]=[CH:40][CH:41]=[N:42]2)(=[O:24])=[O:23])[C:15](N(OC)C)=[O:16])([CH3:10])([CH3:9])[CH3:8]>C(OCC)C.C(OCC)(=O)C>[C:7]([O:11][C:12](=[O:47])[CH2:13][C@H:14]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][C:26]=1[O:34][CH2:35][CH2:36][C:37]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH:39]=[CH:40][CH:41]=[N:42]2)(=[O:24])=[O:23])[CH:15]=[O:16])([CH3:10])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: -65 °C

Procedure

To a −65° C. solution of lithium aluminum hydride (0.51 mL, 1M in diethyl ether) in diethyl ether (5 mL) was added a solution of 3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester (0.10 g, 0.17 mmol) in diethyl ether (5 mL). The reaction was stirred at −65° C. for 2 h. The reaction was then diluted with ethyl acetate (100 mL) and washed with 10% potassium hydrogen sulfate and then saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield (S)-3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester as a clear oil. MS(APCI) m/z 528.1 (M−H).

Workup

washwashed with 10% potassium hydrogen sulfate
dry with materialsaturated sodium chloride, dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e45446fdc60643cab1bff48cff83c68c
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875765B2

Reaction notes

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