Barium hydroxide, monohydrate → (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-(5-methyl-2-(pent-4-enyl)benzylamino)butan-2-ol

HRID 501723

Reaction equation

FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH:35]C(=O)OCC2C=CC=CC=2)[C@H:18]([OH:34])[CH2:19][NH:20][CH2:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=2[CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH:12]=[C:13]([F:15])[CH:14]=1.O.[OH-].[Ba+2].[OH-]>COCCOC.O>[NH2:35][C@@H:17]([CH2:16][C:11]1[CH:12]=[C:13]([F:15])[CH:14]=[C:9]([F:8])[CH:10]=1)[C@H:18]([OH:34])[CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33]

Participants

Conditions

Temperature: 110 °C

Procedure

Step AL (2): To a solution of benzyl (2S,3R)-1-(3,5-difluorophenyl)-3-hydroxy-4-(5-methyl-2-(pent-4-enyl)benzylamino)butan-2-ylcarbamate trifluoroacetate salt (65 mg, 0.102 mmol) in DME (7.0 mL) and water (4.5 mL) was added barium hydroxide monohydrate (625 mg, 3.3 mmol). The reaction mixture was stirred at 110° C. in a high pressure vial for 18 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuum. The residue was purified by reverse phase chromatography to give (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-(5-methyl-2-(pent-4-enyl)benzylamino)butan-2-ol double trifluoroacetate salt (22 mg, 35%) as a colorless oil. LC-MS (M+H)+=389.63.

Workup

filtrationThe reaction mixture was filtered through a pad of celite
concentrationthe filtrate was concentrated in vacuum
customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-d177d3aa82f44c129f1fc318cfe66f6d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772221B2

Linked notes

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