Barium hydroxide, monohydrate → HCID 59423821, compound

HRID 501725Notes

Reaction equation

HRID 501725 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:11][CH2:12][C@H:13]([NH:18][CH2:19][C@@H:20]([OH:42])[C@@H:21]([NH:31]C(=O)OCC1C=CC=CC=1)[CH2:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=1)[CH2:14][CH:15]([CH3:17])[CH3:16])[CH:9]=[CH2:10].O.[OH-].[Ba+2].[OH-]>COCCOC.O>[CH2:8]([O:11][CH2:12][C@H:13]([NH:18][CH2:19][C@@H:20]([OH:42])[C@@H:21]([NH2:31])[CH2:22][C:23]1[CH:24]=[C:25]([F:30])[CH:26]=[C:27]([F:29])[CH:28]=1)[CH2:14][CH:15]([CH3:16])[CH3:17])[CH:9]=[CH2:10]

Participants

5

Reactant 2

HCID 17749100Barium hydroxide, monohydrateHCID 86622350HCID 86622350, compound

Product 1

HCID 59423821HCID 59423821, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

Step AO (2): To a solution of benzyl (2S,3R)-4-((R)-1-(allyloxy)-4-methylpentan-2-ylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate trifluoroacetate salt (560 mg, 1.19 mmol) in DME (9.0 mL) and water (6.0 mL) was added barium hydroxide monohydrate (1.35 g, 7.11 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)-1-((R)-1-(allyloxy)-4-methylpentan-2-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol double trifluoroacetate salt (243 mg, 57%) as a colorless oil. LC-MS (M+H)+=357.09.

Workup

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

Sources & evidence

ORD record
ord-19a91d3e980b42beaebc1f992c3121b7
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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