(Diethylamino)sulfur trifluoride → HCID 131733201, compound

HRID 1527384Notes

Reaction equation

HRID 1527384 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([C:14]([CH3:22])([CH3:21])[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])(O)[CH2:10][C@H:9]1[C:23](=[O:34])[NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[F:33])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:41])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([C:14]([CH3:22])([CH3:21])[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])([F:41])[CH2:10][C@H:9]1[C:23](=[O:34])[NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[F:33])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 131733202HCID 131733202, compound

Product 1

HCID 131733201HCID 131733201, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-(3-chloro-2-fluoro-benzyl carbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (200 mg, 0.35 mmol) in CH2Cl2 (10 mL) under N2 atmosphere at −78° C. was added DAST (92 μL, 0.7 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 to give the desired material which was used without further purification in the next step. TLC, Rf (c-hexane/EtOAc 1:1)=0.75; MS (LC/MS): 541.2/543.1 [M+Na]+, 463.1/465.1 [MH−tBu]+, 419.0/421.1 [MH−Boc]+; tR (HPLC conditions f): 2.81 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

Sources & evidence

ORD record
ord-af0d58b1465b4c3e9eed1922f803da8d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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