Hydrochloric Acid → HCID 67202556, compound

HRID 1429109Notes

Reaction equation

HRID 1429109 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:16]2[C:11](=[C:12]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[C:13]([O:19]C)=[C:14]([O:17]C)[CH:15]=2)[CH:10]=[C:9]([CH3:30])[C:8]=1[C:31]1[C:40]([CH3:41])=[CH:39][C:38]2[C:33](=[CH:34][C:35]([O:53]C)=[C:36]([O:51]C)[C:37]=2[CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=2)[C:32]=1[O:55]C.Cl>C(Cl)Cl>[CH3:41][C:40]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35]([OH:53])[C:36]([OH:51])=[C:37]2[CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=2)=[C:32]([OH:55])[C:31]=1[C:8]1[C:7]([OH:6])=[C:16]2[C:11](=[CH:10][C:9]=1[CH3:30])[C:12]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=1)=[C:13]([OH:19])[C:14]([OH:17])=[CH:15]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 67201660HCID 67201660, compound

Product 1

HCID 67202556HCID 67202556, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 mL of BBr3 solution (5.56 g, 22.2 mmol) was added dropwise into a solution of 15f (1.23 g, 1.76 mmol) in 60 mL of anhydrous CH2Cl2 at −78° C. Stirring was continued at −78° C. for 1 h, 0° C. for 1 h, and ambient temperature for 1 h, respectively. 300 grams of ice containing 30 mL of 6M HCl was added to the mixture and stirred for 0.5 h at room temperature. The aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with water, brine and dried over MgSO4. The solvent was concentrated in vacuo and the residue was purified by C-18 column chromatography (H2O/Acetonitrile) to give 1.1 g of compound 2f (90%) as white solid. Yield, 45%; NMR (600 MHz, CD3OD) δ 7.45 (s, 2H), 7.34 (s, 2H), 7.20 (d, J=7.2 Hz, 4H), 7.08 (d, J=7.2 Hz, 4H), 3.27 (m, 4H), 2.87 (m, 4H), 2.31 (s, 6H), 2.03 (s, 6H). HPLC purity 96.6%, tR=17.00 min (Method A). HRMS calcd for C40H38O6 615.2741 (M+H). found 615.2720.

Workup

  1. waitambient temperature for 1 h
  2. stirringstirred for 0.5 h at room temperature
  3. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationThe solvent was concentrated in vacuo
  7. customthe residue was purified by C-18 column chromatography (H2O/Acetonitrile)

Sources & evidence

ORD record
ord-61249dec6a134b33b1dd9f24f4bc9af1
Source dataset
uspto-grants-2015_01
Patent number
US08937193B2

Reaction notes

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