Hydrochloric Acid → HCID 57986952, compound

HRID 1869299Notes

Reaction equation

HRID 1869299 reaction equation
[CH3:1][O:2][C:3]([C@@:5]1([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH2:9][O:8][C@@H](C(C)(C)C)[N:6]1C(OC(C)(C)C)=O)=[O:4].Cl>CO>[CH3:1][O:2][C:3](=[O:4])[C@@:5]([NH2:6])([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66811850HCID 66811850, compound

Product 1

HCID 57986952HCID 57986952, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under N2, to a solution of crude of 11 (1 mmol) in dried MeOH (5 mL) was added dropwise conc.HCl (2 mL) over 1 hr then stirred for overnight. After concentration, the residue was basified with NaHCO3 at 0° C. The mixture was extracted with CH2Cl2 (5×20 mL). The combined extraction were dried over MgSO4, filtered and concentrated. The crude was submitted to silica gel column chromatography (CH2Cl2:MeOH:NH4OH=500:9:1-100:9:1) to give 12 (95%, from 10). [α]D −3.6 (c 1.45, CHCl3); 1H NMR (CDCl3, 400 MHz) δ 2.75 (d, J=13 Hz, 1H), 3.05 (d, J=13 Hz, 1H), 3.56 (d, J=10 Hz, 1H), 3.73 (s, 3H), 3.87 (d, J=10 Hz, 1H), 7.02 (m, 1H), 7.13 (m, 1H), 7.22-7.27 (m, 2H). 13C NMR (CDCl3, 75 MHz) δ 41.5, 52.4, 63.6, 67.7, 127.4, 128.0, 129.8, 129.9, 134.3, 137.5, 175.3; IR (film): 3359, 3300, 3180, 1736, 1083 cm−1; Mass (ESI) 244.02 ([MH]+).

Workup

  1. concentrationAfter concentration
  2. customwas basified with NaHCO3 at 0° C
  3. extractionThe mixture was extracted with CH2Cl2 (5×20 mL)
  4. extractionThe combined extraction
  5. dry with materialwere dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-997be2d1d0114816bbf03ddb8a883960
Source dataset
uspto-grants-2009_12
Patent number
US07638544B2

Reaction notes

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