Hydrochloric Acid → HCID 441075, compound

HRID 571436Notes

Reaction equation

HRID 571436 reaction equation
[H-].[Na+].C(S)C.C[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:17]=[CH:16][CH:15]=[C:14]([C@@H:18]([OH:29])[C@H:19]3[N:24]4[CH2:25][C@H:26]([CH:27]=[CH2:28])[C@@H:21]([CH2:22][CH2:23]4)[CH2:20]3)[C:12]=2[CH:13]=1.Cl>CCCCCC.CN(C=O)C>[CH2:28]=[CH:27][C@@H:26]1[CH:21]2[CH2:20][C@@H:19]([C@H:18]([OH:29])[C:14]3[CH:15]=[CH:16][N:17]=[C:11]4[C:12]=3[CH:13]=[C:8]([OH:7])[CH:9]=[CH:10]4)[N:24]([CH2:23][CH2:22]2)[CH2:25]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 3034034Quinine

Product 1

HCID 441075HCID 441075, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

NaH (60% in mineral oil, 800 mg, 20.0 mmol, 10.0 equiv) was washed with hexane, dried, and suspended in DMF (20 mL). To this suspension at 0° C. was added ethanethiol (2.96 mL, 40.0 mmol, 20.0 equiv) dropwise over 5 min. The reaction mixture was stirred at 23° C. for 10 min before the addition of quinine (649 mg, 2.00 mmol, 1.00 equiv) in DMF (10 mL) and further stirred for 13 hr at 100° C. The reaction mixture was cooled to 23° C. and neutralized with aqueous 1N HCl. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organic phases were washed with brine (50 mL) and dried (K2CO3). The filtrate was concentrated in vacuo and the residue was triturated with Et2O to afford 580 mg of the title compound as a colorless solid (93% yield).

Workup

  1. customdried
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
  4. washThe combined organic phases were washed with brine (50 mL)
  5. dry with materialdried (K2CO3)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-7f55394349ef4206b1d223d2907cb208
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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