(Diethylamino)sulfur trifluoride → HCID 86673837, compound

HRID 1527389Notes

Reaction equation

HRID 1527389 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([CH2:14][N:15]=[N+:16]=[N-:17])(O)[CH2:10][C@H:9]1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:36])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][N:15]=[N+:16]=[N-:17])([F:36])[CH2:10][C@H:9]1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 86673836HCID 86673836, compound

Product 1

HCID 86673837HCID 86673837, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-4-azidomethyl-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (430 mg, 1.0 mmol) in CH2Cl2 (25 mL) under N2 atmosphere at −78° C. was added DAST (266 μL, 2.01 mmol). The reaction mixture was allowed to warm up to RT and further stirred for 1.5 h. The reaction mixture was poured into an aqueous saturated solution of NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1) to give the desired material. MS (LC/MS): 474.1/476.2 [M+H]+, 472.1 [M−H]−; tR (HPLC conditions f): 2.23 min, 19F NMR (100 MHz, DMSO-d6) δ (ppm): −120, −150.

Workup

  1. extractionextracted twice with CH2Cl2
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-567a097fb8464bf5920d0424079533ad
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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