Hydrochloric Acid → Ethyl 4-([1,1'-biphenyl]-2-yl)-4-amino-2-methylbutanoate

HRID 594355Notes

Reaction equation

[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([NH:16]S(C(C)(C)C)=O)[CH2:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].Cl.O1CCOCC1>CO>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([NH2:16])[CH2:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) slightly yellow solution of ethyl 4-([1,1′-biphenyl]-2-yl)-4-(1,1-dimethylethylsulfinamido)-2-methylbutanoate (220 mg; 0.54 mmol) in MeOH (3 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (0.27 ml; 1.08 mmol). The resulting yellow mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 1 h. The reaction mixture was then concentrated to dryness under reduced pressure and the oily residue was further dried under HV to give the chlorhydrate salt of ethyl 4-([1,1′-biphenyl]-2-yl)-4-amino-2-methylbutanoate. LC-MS (conditions A): tR=0.63 min.; [M+H]+: 298.22 g/mol.

Workup

waitat rt for 1 h
concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
customthe oily residue was further dried under HV

Sources & evidence

ORD record: ord-d2e3b08f030840b391ebfbf2f89b644c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

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