Hydrochloric Acid → HCID 90388346, compound

HRID 2201737Notes

Reaction equation

HRID 2201737 reaction equation
[CH3:1][C@@:2]12[C:18]([C:19]#[N:20])=[CH:17][CH2:16][C@@H:15]1[CH2:14][C@@H:13]1[C@H:4]([CH2:5][CH2:6][C@H:7]3[C@@:12]1([CH3:21])[CH2:11][CH2:10][C@H:9]([O:22]COC)[CH2:8]3)[CH2:3]2.Cl>CO.ClCCl>[CH3:1][C@@:2]12[C:18]([C:19]#[N:20])=[CH:17][CH2:16][C@@H:15]1[CH2:14][C@@H:13]1[C@H:4]([CH2:5][CH2:6][C@H:7]3[C@@:12]1([CH3:21])[CH2:11][CH2:10][C@H:9]([OH:22])[CH2:8]3)[CH2:3]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90388611HCID 90388611, compound

Product 1

HCID 90388346HCID 90388346, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To compound 26 (125 mg, 0.36 mmol) in methanol (9 mL) and dichloromethane (3 mL) was added 6 N HCl (10 ml) at room temperature. After 14 h, the mixture was extracted with dichloromethane (50 mL×2). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) to afford compound 27 (101 mg, 93%): mp 170-172° C., [α]D25+5.4 (c 0.24, CHCl3); 1H NMR (CDCl3) δ 6.61 (t, J=2.8 Hz, 1H), 4.04-4.02 (m, 1H), 0.89 (s, 3H), 0.78 (s, 3H); 13C NMR (CDCl3) δ 147.7, 127.3, 116.0, 66.3, 55.1, 50.5, 48.1, 42.2, 39.1, 36.4, 35.7, 35.0, 34.8, 32.3, 32.0, 28.8, 28.7, 22.4, 16.6, 11.1; IR νmax 3391, 2216, 1448 cm−1. Anal. Calcd for (C20H29NO): C, 80.22; H, 9.76; N, 4.68. Found: C, 80.32; H, 9.70; N, 4.72.

Workup

  1. extractionthe mixture was extracted with dichloromethane (50 mL×2)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-633acb6e11284f7faf5ffbcc2f1e3a40
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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