Dichloromethane → HCID 10298481, compound

HRID 719672Notes

Reaction equation

HRID 719672 reaction equation
[C:1]([C@@H:3]1[CH2:7][C@H:6]([F:8])[CH2:5][N:4]1[C:9]([C@@H:11]([NH:30]C(=O)OC(C)(C)C)[C:12]([CH3:29])([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)[CH3:13])=[O:10])#[N:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+].C(Cl)[Cl:51]>>[ClH:51].[NH2:30][C@@H:11]([C:12]([CH3:29])([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)[CH3:13])[C:9]([N:4]1[CH2:5][C@@H:6]([F:8])[CH2:7][C@H:3]1[C:1]#[N:2])=[O:10]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86594192HCID 86594192, compound

Product 1

HCID 10298481HCID 10298481, compound

Procedure

To a CH2Cl2 solution (45 mL) containing tert-butyl (1R)-1-{[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]carbonyl}-2-methyl-2-[(3-phenoxybenzyl)thio]propylcarbamate (500 mg, 0.0010 mol) was added TFA (5 mL). The reaction mixture was allowed to stir at RT for a period of 16.0 hours followed by neutralization with sat. NaHCO3. The organics were separated, dried over MgSO4 and concentrated to dryness to afford a crude solid. The resulting solid was purified using silica gel chromatography (99% CH2Cl2/1% MeOH with 2.0 M NH3). The pure solid was dissolved into an acetone/ether mixture (1/1) and precipitated using 2.0 N HCl in ether. The resulting solid was filtered in vacuo and washed with ether. After drying under high vacuum the reaction yielded a total of 132 mg of the title compound.

Workup

  1. customThe organics were separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness
  4. customto afford a crude solid
  5. customThe resulting solid was purified
  6. dissolutionThe pure solid was dissolved into an acetone/ether mixture (1/1)
  7. customprecipitated
  8. filtrationThe resulting solid was filtered in vacuo
  9. washwashed with ether
  10. customAfter drying under high vacuum the reaction

Sources & evidence

ORD record
ord-bfe1f0131040439196e0ff80e743cd24
Source dataset
uspto-grants-2006_11
Patent number
US07132443B2

Reaction notes

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