Hydrochloric Acid → HCID 11475844, compound

HRID 646802Notes

Reaction equation

HRID 646802 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C:5]([CH3:40])([CH3:39])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([N+]#[C-])(S(C1C=CC(C)=CC=1)(=O)=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2].Cl.[OH2:43]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:41])[C:5]([CH3:40])([CH3:39])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:43])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11387750HCID 11387750, compound

Product 1

HCID 11475844HCID 11475844, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 208i (12.0 g, 20.3 mmol) in CH2Cl2 (200 mL) was added concd HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature and diluted with water (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 209i (3.5 g, 40.0%) as a colorless oil. 1H NMR (CDCl3): δ (ppm): 4.14 (q, J=7.1, 4H), 2.41 (t, J=7.0, 4H), 1.66-1.45 (m, 8H), 1.35-1.20 (m, 12H), 1.25 (t, J=7.1, 6H), 1.17 (s, 12H). 13C NMR (CDCl3): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423, found: 427.3430.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×70 mL)
  3. washThe combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customto yield the crude product (7.52 g)
  7. customPurification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)

Sources & evidence

ORD record
ord-b5b9ffa1d1e1485d9a553245ec70cbff
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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