(Diethylamino)sulfur trifluoride → HCID 178453975, compound

HRID 2221025Notes

Reaction equation

HRID 2221025 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12](O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:22])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([F:22])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanol

Product 1

HCID 178453975HCID 178453975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (t-butoxy)-N-(4-hydroxycyclohexyl)carboxamide (1 equivalent) in CH2Cl2 (1 M) cooled to −78° C. was added dropwise a solution of DAST (1 equivalent) in CH2Cl2 (0.5 M). The mixture was stirred at −78° C. for 4 hours, and then allowed to rise to room temperature. The solution was poured into saturated NaHCO3 and extracted with chloroform, dried, and evaporated. The resulting crude product was purified on silica gel, eluting with ethyl acetate/hexane 5:95.

Workup

  1. customto rise to room temperature
  2. extractionextracted with chloroform
  3. customdried
  4. customevaporated
  5. customThe resulting crude product was purified on silica gel
  6. washeluting with ethyl acetate/hexane 5:95

Sources & evidence

ORD record
ord-0312867a9ca3454f8c6a4185b220d809
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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