(Diethylamino)sulfur trifluoride → HCID 68284000, compound

HRID 1527385Notes

Reaction equation

HRID 1527385 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11](O)([CH3:13])[CH2:10][C@H:9]1[C:15](=[O:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[F:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:33])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:33])([CH3:13])[CH2:10][C@H:9]1[C:15](=[O:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[F:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 68283044HCID 68283044, compound

Product 1

HCID 68284000HCID 68284000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (865 mg, 2.1 mmol) in CH2Cl2 (60 mL) under nitrogen at −78° C. was added DAST (550 μL, 4.16 mmol) and the solution was slowly allowed to reach RT and stirred for 1 h. The reaction mixture was poured into cold aqueous saturated NaHCO3 solution and extracted with CH2Cl2 (×2). The combined organic layers were dried (Na2SO4), filtered and concentrated to give the desired material which was used in the next step without further purification. TLC, Rf (EtOAc)=0.75; MS (UPLC/MS): 389.3/391.3 [M+H]+, 411.3/413.2 [M+Na]+, 333.2/335. [MH−tBu]+, 289.2/291.2 [MH−Boc]+, 387.2/389.4 [M−H]−, 433./435.2 [M+HCOO]−; tR (HPLC conditions f): 2.2 min.

Workup

  1. customto reach RT
  2. extractionextracted with CH2Cl2 (×2)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-318000ab168042709ee1258fa000ce0e
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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