1,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(methylamino)butanoate → Methyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(methylamino)butanoate, hydrochloride

HRID 1160397Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH3:22])[CH2:12][C:13]([O:15][C:16](C)(C)C)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]>CO.Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH3:22])[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

Conditions

Temperature: 60 °C

Procedure

The 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(methylamino)butanoate from the previous step (31.4 g) was dissolved in a mixture of MeOH (100 mL) and 4N HCl/dioxane (30 mL) and heated to 60° C. for 1.25 h. The solvents were concentrated to a slurry, Et2O (200 mL) was added, the solid filtered, washed well with Et2O to give the titled compound (15.6 g).

Workup

concentrationThe solvents were concentrated to a slurry, Et2O (200 mL)
additionwas added
filtrationthe solid filtered
washwashed well with Et2O

Sources & evidence

ORD record: ord-9cfef89d7617450e80e24c73c4cdc4ed
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816395B2

Reaction notes

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