Hydrochloric Acid → HCID 89723053, compound

HRID 2178148Notes

Reaction equation

HRID 2178148 reaction equation
CC([S@@]([NH:7][C@:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])([CH2:12][C@H:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[CH:9]([F:11])[F:10])=O)(C)C.Cl>CO>[NH2:7][C@@:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])([CH:9]([F:11])[F:10])[CH2:12][C@H:13]([OH:18])[C:14]([F:17])([F:16])[F:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117833547HCID 117833547, compound

Product 1

HCID 89723053HCID 89723053, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate XVIII-1: Under an inert atmosphere a solution of (S)-2-methyl-N-((2S,4S)-1,1,5,5,5-pentafluoro-2-(2-fluorophenyl)-4-hydroxypentan-2-yl)propane-2-sulfinamide (XVII-2) (261 mg, 0.667 mmol) and hydrochloric acid (4 M in dioxane, 0.667 ml, 2.67 mmol) in MeOH (5 ml) was stirred at 25° C. After 4 h the solvent was removed at reduced pressure. The residue was treated with a half-saturated solution of Na2CO3 and extracted three times with AcOEt. The combined organic layers were dried over MgSO4 and evaporated at reduced pressure. The crude product was purified by chromatography on silica gel (eluent: heptane/AcOEt 10:1) to yield the (2S,4S)-4-amino-1,1,1,5,5-pentafluoro-4-(2-fluorophenyl)pentan-2-ol (XVIII-1) (168 mg, 87.7%) as a light yellow solid. MS: m/z=288.5 (M+H)+.

Workup

  1. customAfter 4 h the solvent was removed at reduced pressure
  2. additionThe residue was treated with a half-saturated solution of Na2CO3
  3. extractionextracted three times with AcOEt
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated at reduced pressure
  6. customThe crude product was purified by chromatography on silica gel (eluent: heptane/AcOEt 10:1)

Sources & evidence

ORD record
ord-01d2a0e0c9484cf39cc4c0caff2703c0
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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