Hydrochloric Acid → HCID 59820019, compound

HRID 553572Notes

Reaction equation

HRID 553572 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([O:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[B:32]2[O:36]C(C)(C)C(C)(C)[O:33]2)[CH2:17]1.Cl>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([O:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[B:32]([OH:33])[OH:36])[CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12146331HCID 12146331, compound

Product 1

HCID 59820019HCID 59820019, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Unpurified (1S,3R)-5-methyl-4-(3-{2-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenoxy]ethoxy}cyclohexyloxymethyl)-2-m-tolyloxazole is taken up in 6 ml of THF, and 0.75 ml of 1N HCl is added. After 3 h of stirring at room temperature, the solvent is evaporated and the residue is taken up in DMF then purified by RP-HPLC. This gives (1R,3S)-2-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy}phenylboronic acid as a colorless oil. 465.36 (C26H32BNO6), MS (ESI): 466 (M+H+).

Workup

  1. customthe solvent is evaporated
  2. customthen purified by RP-HPLC

Sources & evidence

ORD record
ord-14fc1c0036904fa9bf3cc7a98c423fd6
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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