Methanol → HCID 89922853, compound

HRID 921931Notes

Reaction equation

HRID 921931 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10](=[O:13])[CH2:11][OH:12])=[CH:6][C:5]([C:14]#[N:15])=[CH:4][C:3]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].CO.[BH4-].[Na+].[S:28](Cl)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:35][C:34]1[CH:36]=[CH:37][C:31]([S:28]([O:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8][C:7]2[CH:6]=[C:5]([C:14]#[N:15])[CH:4]=[C:3]([NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:23])[C:2]=2[Cl:1])(=[O:30])=[O:29])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 73974-Toluenesulfonyl chlorideHCID 4311764Sodium borohydrideHCID 131734954HCID 131734954, compound

Product 1

HCID 89922853HCID 89922853, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottom flask was added tert-butyl (2-chloro-5-cyano-3-(4-hydroxy-3-oxobutyl)phenyl)carbamate (500 mg, 1.476 mmol) and MeOH (1 mL). The solution was then cooled to 0° C. before NaBH4 (100 mg) was added. The reaction was then stirred at 0° C. for 30 min and then slowly warmed to room temperature, and stirred for additional 1 h. The reaction was then quenched with aq. NaHCO3, extracted with EtOAc, washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was then dissolved in DCM (10 mL). Pyridine (1 mL) was added. After the reaction was cooled to 0° C. Ts-Cl (310 mg, 1.623 mmol) was added, and the reaction was then allowed to warm to room temperature and stirred for 5 h. The reaction was then taken up with DCM, washed with brine, and concentrated in vacuo to give 4-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)-2-hydroxybutyl 4-methylbenzenesulfonate (810 mg) as a yellow solid.

Workup

  1. additionwas added
  2. temperatureslowly warmed to room temperature
  3. stirringstirred for additional 1 h
  4. customThe reaction was then quenched with aq. NaHCO3
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was then dissolved in DCM (10 mL)
  10. additionPyridine (1 mL) was added
  11. temperatureAfter the reaction was cooled to 0° C
  12. temperatureto warm to room temperature
  13. stirringstirred for 5 h
  14. washwashed with brine
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f665def4961541cca54fde7360575503
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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