(Diethylamino)sulfur trifluoride → HCID 178453975, compound

HRID 1796991Notes

Reaction equation

HRID 1796991 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-96ece0999a374ada9350a9d7af8056fa
Source dataset
uspto-grants-2006_04
Patent number
US07034033B2

Reaction notes

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