(Diethylamino)sulfur trifluoride → HCID 68283698, compound

HRID 1527387Notes

Reaction equation

HRID 1527387 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11](O)([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:21](=[O:32])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[F:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:39])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:39])([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:21](=[O:32])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[F:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 68283902HCID 68283902, compound

Product 1

HCID 68283698HCID 68283698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-4-morpholin-4-ylmethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (85 mg, 0.18 mmol) in CH2Cl2 (10 mL) under N2 atmosphere at −78° C. was added DAST (47 μL, 0.359 mmol). The reaction mixture was then allowed to reach RT and further stirred for 1.5 h then 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 (CH2Cl2/MeOH 8:2) to give the desired material. MS (LC/MS): 474.1/476.2 [M+H]+, 472.1 [M−H]−; tR (HPLC conditions f): 1.59 min.

Workup

  1. customto reach RT
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography on silica gel (CH2Cl2/MeOH 8:2)

Sources & evidence

ORD record
ord-47ba01c2843d41a8acca6d6919088bb7
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…