Hydrochloric Acid → HCID 11475844, compound

HRID 1466711Notes

Reaction equation

HRID 1466711 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 9-isocyano-2,2,16,16-tetramethyl-9-(toluene-4-sulfonyl)-heptadecanedioic acid diethyl ester (12.0 g, 20.3 mmol) in methylene chloride (200 mL) was added concd HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature. The mixture was diluted with water (200 mL), the layers were separated, and the aqueous layer was extracted with methylene chloride (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL). The solution was dried over 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 2,2,16,16-tetramethyl-9-oxoheptadecanedioic acid diethyl ester (3.5 g, 40%) as a colorless oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 4.14 (q, J=7.1 Hz, 4H), 2.41 (t, J=7.0 Hz, 4H), 1.66-1.35 (m, 20H), 1.25 (t, J=7.1 Hz, 6H), 1.17 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): 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 methylene chloride (3×70 mL)
  3. washThe combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL)
  4. dry with materialThe solution was dried over 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-12ad4e48a7ad41d9904d959899347234
Source dataset
uspto-grants-2015_04
Patent number
US09000041B2

Reaction notes

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