Hydrochloric Acid → HCID 87952601, compound

HRID 1814276Notes

Reaction equation

HRID 1814276 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[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1)(=[O:24])=[O:23])[C:15](N(OC)C)=[O:16])([CH3:10])([CH3:9])[CH3:8].OS([O-])(=O)=O.[K+].Cl>CCOCC.O1CCCC1.C(OCC)(=O)C.CCCCCC>[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[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1)(=[O:23])=[O:24])[CH:15]=[O:16])([CH3:8])([CH3:9])[CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 86588195HCID 86588195, compound

Product 1

HCID 87952601HCID 87952601, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-65 °C

Procedure

A solution of lithium aluminum hydride (1.45 mL, 1.0 M in ether) was added in 3 portions over a period of 35 minutes to a solution of 3-(4-acetylamino-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (270 mg, 0.45 mmol) in dry ether (12 mL) and tetrahydrofuran (2 mL) at −65° C. under an atmosphere of dry nitrogen. The reaction mixture was stirred at −65° C. for an additional 10 minutes followed by the careful, dropwise addition of 0.3 N KHSO4 (10 mL) at −65° C. The reaction mixture was allowed to warm to room temperature and 0.1 N HCl (20 mL) was added. The organic layer was collected, dried (MgSO4) and evaporated to give the crude aldehyde (230 mg). Flash chromatography (silica, 2:1 ethyl acetate/hexane) provided pure 3-[4-acetylamino-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester (140 mg).

Workup

  1. temperatureto warm to room temperature
  2. customThe organic layer was collected
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give the crude aldehyde (230 mg)

Sources & evidence

ORD record
ord-fed2e3784dca4f74b086d79cec4bf6e5
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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