Hydrochloric Acid → HCID 44224066, compound

HRID 451647Notes

Reaction equation

HRID 451647 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:16]2[CH:15]=[C:14]([O:17]C)[C:13]([O:19]C)=[C:12]([C:21]([NH:23][CH2:24][CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])=[O:22])[C:11]=2[CH:10]=[C:9]([CH3:33])[C:8]=1[C:34]1[C:43]([CH3:44])=[CH:42][C:41]2[C:40]([C:45]([NH:47][CH2:48][CH:49]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH3:50])=[O:46])=[C:39]([O:57]C)[C:38]([O:59]C)=[CH:37][C:36]=2[C:35]=1[O:61]C.Cl>C(Cl)Cl>[OH:6][C:7]1[C:16]2[CH:15]=[C:14]([OH:17])[C:13]([OH:19])=[C:12]([C:21]([NH:23][CH2:24][CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])=[O:22])[C:11]=2[CH:10]=[C:9]([CH3:33])[C:8]=1[C:34]1[C:43]([CH3:44])=[CH:42][C:41]2[C:40]([C:45]([NH:47][CH2:48][CH:49]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH3:50])=[O:46])=[C:39]([OH:57])[C:38]([OH:59])=[CH:37][C:36]=2[C:35]=1[OH:61]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 44191538HCID 44191538, compound

Product 1

HCID 44224066HCID 44224066, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.45 mL of BBr3 solution (1.18 g, 4.73 mmol) was added dropwise into a solution of compound 8 (310 mg, 0.40 mmol) in 20 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. 50 grams of ice containing 10 mL of 6M HCl was added to the mixture and stirred for 1 h at room temperature. The aqueous layer was extracted with dichloromethane (3×50 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 using C-18 column chromatography (H2O/Acetonitrile) to give 200 mg of compound 10 (72%) as white-yellow solid. 1H NMR (600 MHz, CD3OD) δ 7.56 (d, J=6.6 Hz, 2H), 7.39 (t, J1=6.0 Hz, J2=3.0 Hz, 4H), 7.35 (t, J1=6.0 Hz, J2=6.6 Hz, 4H), 7.23 (t, J1=6.0 Hz, J2=6.6 Hz, 2H), 7.06 (s, 1H), 6.99 (s, 1H), 3.76 (dd, J1=6.6 Hz, J2=11.4 Hz, 1H), 3.68 (m, 3H), 3.22 (m, 2H), 1.90 (s, 3H), 1.89 (s, 3H), 1.43 (m, 6H). HRMS calcd for C42H40N2O8 701.2857 (M+H), found 701.2853. 150 mg of compound 10 was further purified using a CHIRALCEL OD-RH 5 μM 250 mm×10 mm reverse phase chiral column to give 50 mg of compound 13 and 58 mg of compound 14, respectively.

Workup

  1. waitambient temperature for 1 h
  2. stirringstirred for 1 h at room temperature
  3. extractionThe aqueous layer was extracted with dichloromethane (3×50 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

Sources & evidence

ORD record
ord-7999d0f403654d5da7bb2beb9b35aeb0
Source dataset
uspto-grants-2013_07
Patent number
US08487131B2

Reaction notes

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