Hydrochloric Acid → Methyl 5-amino-5-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pentanoate

HRID 594349Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][O:4][C:3]2[C:7]([CH:11]([NH:19]S(C(C)(C)C)=O)[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:8][CH:9]=[CH:10][C:2]1=2.Cl.O1CCOCC1>CO>[NH2:19][CH:11]([C:7]1[C:3]2[O:4][CH2:5][CH2:6][O:1][C:2]=2[CH:10]=[CH:9][CH:8]=1)[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) slightly yellow solution of methyl 5-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate (160 mg; 0.43 mmol) in MeOH (2 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (0.22 ml; 0.88 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 yellow oily residue was further dried under HV to give the chlorhydrate salt of methyl 5-amino-5-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pentanoate as a yellow solid. LC-MS (conditions A): tR=0.47 min.; [M+H]+: 266.11 g/mol.

Workup

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

Sources & evidence

ORD record: ord-0b94416845ae4930917c1b94a77d39c3
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242970B2

Reaction notes

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