Hydrochloric Acid → HCID 117974129, compound

HRID 1776115Notes

Reaction equation

HRID 1776115 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[C@@H:12]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:11]([CH3:32])[O:10][C:9]1=[O:33])(C)(C)C.[ClH:35].O1CCOCC1>C(Cl)Cl>[Cl-:35].[CH3:32][C@@H:11]1[O:10][C:9](=[O:33])[C@@H:8]([NH3+:7])[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[C@H:12]1[O:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 117982178HCID 117982178, compound

Product 1

HCID 117974129HCID 117974129, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL screw top vial was charged with tert-butyl((3S,7R,8R,9S)-9-methyl-7-(4-methylbenzyl)-2-oxo-8-phenoxyoxonan-3-yl)carbamate (300 mg, 0.642 mmol), anhydrous CH2Cl2 (4 mL), and 4.0 M HCl in dioxane (3.21 mL, 12.83 mmol). After stirring at room temperature for 80 min, the reaction mixture was concentrated under a stream of nitrogen and dried under high vacuum to provide the title compound as a beige solid (259 mg, 100%): mp 200-210° C. (dec.); 1H NMR (400 MHz, CDCl3) δ 7.46-6.81 (m, 9H), 5.14 (s, 1H), 3.78-3.52 (m, 3H), 2.86 (s, 1H), 2.60-1.12 (m, 12H), 0.96 (s, 1H); 13C NMR (101 MHz, CD3OD) δ 171.05, 160.65, 137.89, 136.19, 130.75, 129.87, 129.75, 122.14, 117.03, 81.89, 76.55, 68.05, 46.67, 37.46, 32.38, 27.71, 21.05, 20.12, 18.85; ESIMS m/z 369 ([M+H]+).

Workup

  1. concentrationthe reaction mixture was concentrated under a stream of nitrogen
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-8afa1a0104574a5da2f95368fe8c0399
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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