Hydrochloric Acid → HCID 78323391, compound

HRID 2201728Notes

Reaction equation

HRID 2201728 reaction equation
COC[O:4][C@@H:5]1[CH2:18][C@@H:17]2[C@H:8]([C@H:9]3[C@H:14]([CH2:15][CH2:16]2)[CH2:13][C@:12]2([CH3:24])[C@@H:19]([C:22]#[N:23])[CH2:20][CH2:21][C@H:11]2[CH2:10]3)[CH2:7][CH2:6]1.Cl>CO.ClCCl>[OH:4][C@@H:5]1[CH2:18][C@@H:17]2[C@H:8]([C@H:9]3[C@H:14]([CH2:15][CH2:16]2)[CH2:13][C@:12]2([CH3:24])[C@@H:19]([C:22]#[N:23])[CH2:20][CH2:21][C@H:11]2[CH2:10]3)[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90388581HCID 90388581, compound

Product 1

HCID 78323391HCID 78323391, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To compound 9 (165 mg, 0.5 mmol) in methanol (9 mL) and dichloromethane (3 mL) was added 6 N HCl (10 ml) at room temperature. After 14 h, the product was extracted into EtOAc (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 10 (135 mg, 94%): mp 162-164° C.; [α]D20 +33.9 (c 0.31, CHCl3); 1H NMR (CDCl3) δ 4.06 (s, br, 1H), 0.86 (s, 3H); 13C NMR (CDCl3) δ 121.3, 66.1, 48.3, 47.9, 46.9, 44.9, 44.2, 40.2, 39.8, 38.1, 36.0, 33.8, 33.7, 32.6, 28.4, 26.3 (2C), 23.1, 14.2; IR νmax 3456, 2235, 1447 cm−1. Anal. Calcd for (C19H29NO): C, 79.39; H, 10.17; N, 4.87. Found: C, 79.60; H, 10.26; N, 4.92.

Workup

  1. extractionthe product was extracted into EtOAc (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-4f085cfe20d8447d85750fe4db2377c8
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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