Tetrahydrofuran → [4-((2S)-2-[(Benzyloxy)carbonyl]amino-3-methoxy-3-oxopropyl)-2-methylphenyl]boronic Acid

HRID 724715Notes

Reaction equation

HRID 724715 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([B:24]2[O:28]C(C)(C)C(C)(C)[O:25]2)=[C:20]([CH3:33])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+].O1CCCC1.C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.Cl.O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([B:24]([OH:28])[OH:25])=[C:20]([CH3:33])[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 11669639Methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoateHCID 23667635Sodium periodate

Product 1

HCID 11632112[4-((2S)-2-[(Benzyloxy)carbonyl]amino-3-methoxy-3-oxopropyl)-2-methylphenyl]boronic AcidYield 100.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate (6.90 g, 15.2 mmol), sodium periodate (16.3 g, 76.1 mmol), tetrahydrofuran (156 mL), ammonium acetate (4.69 g, 60.9 mmol) and water (156 mL) was stirred at 25° C. for 24 h. The reaction was diluted with ethyl acetate and 1 N HCl solution. The aqueous solution was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was crystallized in ethyl acetate to yield the desired product (5.65 g, 80%). 1H NMR (400 MHz, CD3OD): δ 7.3 (m, 5H), 7.16 (d, 1H), 7.0 (m, 2H), 5.02 (m, 2H), 4.42 (m, 1H), 3.68 (s, 3H), 3.10 (m, 1H), 2.88 (m, 1H), 2.28 (s, 3H); MF=C19H22BNO6; LCMS found for C19H23BNO6 (M+H)+: m/z=372.

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate once
  2. washThe combined organic solutions were washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was crystallized in ethyl acetate

Sources & evidence

ORD record
ord-6950f5f64b424b10a4a8ef56f9254ad2
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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