Sodium Hydroxide → HCID 23653901, compound

HRID 1670409Notes

Reaction equation

HRID 1670409 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([NH:13][C:14](=[O:33])[C@@H:15]([C@H:18]3[C@@H:23]([OH:24])[C@@H:22](/[CH:25]=[CH:26]/[C:27]([CH3:30])([CH3:29])[CH3:28])[O:21]C(C)(C)[O:19]3)[O:16][CH3:17])[CH2:8][CH2:7][C:6]=2[CH:34]=1.[OH-].[Na+]>C1COCC1.Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([NH:13][C:14](=[O:33])[C@H:15]([O:16][CH3:17])[C@H:18]([OH:19])[C@@H:23]([OH:24])[C@H:22]([OH:21])/[CH:25]=[CH:26]/[C:27]([CH3:29])([CH3:30])[CH3:28])[CH2:8][CH2:7][C:6]=2[CH:34]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57655897HCID 57655897, compound

Product 1

HCID 23653901HCID 23653901, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

150 mg of 12 (258 μmol) in 1.4 ml of THF and 2.78 ml of 1N hydrochloric acid are introduced into a 25 ml round-bottomed flask, with agitation and under argon. The agitation is maintained for 4.5 h at AT. The medium is neutralized with NaOH (1N), to pH 7, and extracted with 2 times 3 ml of EtOAc. The combined organic phases are dried over MgSO4, filtered and evaporated to dryness. The crude is chromatographed on a silica cartridge (10 g), elution being carried out with CH2Cl2/MeOH (as an MeOH gradient of 1 to 10%). 65 mg of expected product Ex3 are recovered. 40 mg of Ex3 are separated by preparative chiral HPLC (Chirapad AD-H 5 μm 250×4.6 mm, flow rate 1 ml/min, mobile phase: 50% heptane-50% EtOH, 0.1% TEA), to give 9 mg of Ex3a (tr=7.48 min) and 20 mg of Ex3b (tr=9.71 min).

Workup

  1. temperatureThe agitation is maintained for 4.5 h at AT
  2. extractionextracted with 2 times 3 ml of EtOAc
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude is chromatographed on a silica cartridge (10 g), elution
  7. custom65 mg of expected product Ex3 are recovered
  8. custom40 mg of Ex3 are separated by preparative chiral HPLC (Chirapad AD-H 5 μm 250×4.6 mm, flow rate 1 ml/min, mobile phase: 50% heptane-50% EtOH, 0.1% TEA)
  9. customto give 9 mg of Ex3a (tr=7.48 min) and 20 mg of Ex3b (tr=9.71 min)

Sources & evidence

ORD record
ord-f77a7ff7ed1f49ceb904a1c2df02021a
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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