Sodium Hydroxide → HCID 23653902, compound

HRID 1670411Notes

Reaction equation

HRID 1670411 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[NH:16][C:15](=[O:17])[CH:14]([NH:18][C:19](=[O:38])[C@@H:20]([C@H:23]4[C@@H:28]([OH:29])[C@@H:27](/[CH:30]=[CH:31]/[C:32]([CH3:35])([CH3:34])[CH3:33])[O:26]C(C)(C)[O:24]4)[O:21][CH3:22])[CH2:13][CH2:12][C:11]=3[CH:39]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.Cl>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[NH:16][C:15](=[O:17])[CH:14]([NH:18][C:19](=[O:38])[C@H:20]([O:21][CH3:22])[C@H:23]([OH:24])[C@@H:28]([OH:29])[C@H:27]([OH:26])/[CH:30]=[CH:31]/[C:32]([CH3:35])([CH3:33])[CH3:34])[CH2:13][CH2:12][C:11]=3[CH:39]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57655896HCID 57655896, compound

Product 1

HCID 23653902HCID 23653902, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

150 mg of 15 (280 μmol) in 1,4 ml of THF and 2.78 ml of 1N hydrochloric acid are introduced into a 20 ml round-bottomed flask, with stirring and under argon. The stirring is maintained for 4 h at AT. The medium is neutralized with NaOH (1N), to pH 7, and extracted with 2 times 5 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) with an eluent of CH2Cl2/MeOH (as an MeOH gradient of 1 to 10%). 85 mg of expected product Ex4 are recovered. 58 mg of Ex4 are separated by preparative chiral HPLC (Chirapad AD-H 5 μm 250×4.6 mm, flow rate 1 ml/min, mobile phase: 70% heptane-30% EtOH, 0.1% TEA), to give 16 mg of Ex4a (tr=13.42 min) and 40 mg of Ex4b (tr=18.96 min).

Workup

  1. temperatureThe stirring is maintained for 4 h at AT
  2. extractionextracted with 2 times 5 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) with an eluent of CH2Cl2/MeOH (as an MeOH gradient of 1 to 10%)
  7. custom85 mg of expected product Ex4 are recovered
  8. custom58 mg of Ex4 are separated by preparative chiral HPLC (Chirapad AD-H 5 μm 250×4.6 mm, flow rate 1 ml/min, mobile phase: 70% heptane-30% EtOH, 0.1% TEA)
  9. customto give 16 mg of Ex4a (tr=13.42 min) and 40 mg of Ex4b (tr=18.96 min)

Sources & evidence

ORD record
ord-862371d334754c7abbf175ac10db5747
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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