Hydrochloric Acid → HCID 59820054, compound

HRID 553573Notes

Reaction equation

HRID 553573 reaction equation
Cl.[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)=[N:5][C:4]=1[CH2:15][O:16][C@H:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[B:31]2[O:35]C(C)(C)C(C)(C)[O:32]2)[CH2:18]1>C1COCC1>[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)=[N:5][C:4]=1[CH2:15][O:16][C@H:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[B:31]([OH:32])[OH:35])[CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60119087HCID 60119087, compound

Product 1

HCID 59820054HCID 59820054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 ml of 1 N HCl is added to 300 mg of (1S,3R)-5-methyl-4-{3-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyloxy]cyclohexyloxymethyl}-2-m-tolyloxazole in 5 ml of THF, and the mixture is stirred at RT until the reaction has gone to completion. The solvent is removed under reduced pressure and the compound is purified by RP-HPLC. This gives (1R,3S)-2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]benzeneboronic acid as a colorless oil. C25H30BNO5 (435.33), MS (ESI): 436 (M+H+).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe compound is purified by RP-HPLC

Sources & evidence

ORD record
ord-4aaf52fb6cdb45cca4040de559503ad4
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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