Hydrochloric Acid → HCID 90388527, compound

HRID 2201746Notes

Reaction equation

HRID 2201746 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.COCO[C@H]1C[C@H]2[C@@H]([C@@H]3[C@@H](CC2)C[C@@]2(C)C(OS(C(F)(F)F)(=O)=O)=CC[C@@H]2C3)CC1.Cl>CO>[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 3

HCID 313Hydrochloric AcidHCID 90388609HCID 90388609, compoundHCID 90397202HCID 90397202, compound

Product 1

HCID 90388527HCID 90388527, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 50 (250 mg containing the aromatic impurity carried over from compound 48) in methanol (30 mL) was added 6 N HCl (15 mL) at room temperature. After 4 h, the product was extracted into dichloromethane (50 mL×3), and 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 give compound 51 (84 mg): mp. 163-165° C.; [α]D25 −33.9 (c 0.18, CHCl3); 1H NMR (CDCl3) δ 4.06-4.00 (m, 1H), 0.88 (s, 3H); 13C NMR (CDCl3) δ 121.4, 66.2, 48.4, 48.0, 47.0, 45.0, 44.2, 40.3, 39.8, 38.1, 36.0, 33.9, 33.8, 32.7, 28.4, 26.4 (2×C), 23.2, 14.2; IR νmax 3456, 2235 cm−1. Anal. Calcd for (C19H29NO): C, 79.39; H, 10.17. Found: C, 79.16; H, 10.14.

Workup

  1. extractionthe product was extracted into dichloromethane (50 mL×3)
  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-9e602bcb91ee4f30ada94d07054efcc3
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

Loading…