Thionyl Chloride → HCID 72243876, compound

HRID 1807158Notes

Reaction equation

HRID 1807158 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([F:35])=[C:8]([CH:12]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[F:26])([C:17]#[N:18])[CH:15]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[NH:14][CH:13]2[C:32](O)=[O:33])[CH:9]=[CH:10][CH:11]=1.[NH2:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[C:42](=[O:46])[NH:41][C:40]2=[O:47]>C(N(CC)CC)C>[O:46]=[C:42]1[C:43]2[C:39](=[CH:38][C:37]([NH:36][C:32]([CH:13]3[CH:12]([C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[C:7]=4[F:35])[C:16]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[F:26])([C:17]#[N:18])[CH:15]([CH2:27][C:28]([CH3:31])([CH3:29])[CH3:30])[NH:14]3)=[O:33])=[CH:45][CH:44]=2)[C:40](=[O:47])[NH:41]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 729154-AminophthalimideHCID 666882513-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid

Product 1

HCID 72243876HCID 72243876, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of thionyl chloride (2 mL), rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (110 mg, 0.24 mmol) was added and the mixture was stirred at rt for 2 hrs. The excess thionyl chloride was removed and the residue was dissolved in methylene chloride (5 mL) and 5-amino-isoindole-1,3-dione (Aldrich, 0.30 mmol) was added followed by the addition of triethylamine (0.2 mL). The mixture was stirred overnight. The solvent was removed and the residue was purified on an ISCO machine (24 g column, eluent, 40-80% EtOAc/hexanes) to give a pale yellow solid. 10 mg.

Workup

  1. customThe excess thionyl chloride was removed
  2. dissolutionthe residue was dissolved in methylene chloride (5 mL)
  3. stirringThe mixture was stirred overnight
  4. customThe solvent was removed
  5. customthe residue was purified on an ISCO machine (24 g column, eluent, 40-80% EtOAc/hexanes)
  6. customto give a pale yellow solid

Sources & evidence

ORD record
ord-406c177b193d4a869f48a3fd55ecbe97
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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