HCID 68703262, compound → HCID 86607260, compound

HRID 1437385Notes

Reaction equation

HRID 1437385 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][C@@H:11]([C:14](=[O:27])[NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]3)[CH2:10][C@H:9]1[O:28][CH3:29])(C)(C)C>ClCCl>[CH3:26][C:23]1[CH:22]=[CH:21][C:20]2[C:25](=[C:16]([NH:15][C:14]([C@@H:11]3[CH2:12][CH2:13][C@@H:8]([NH2:7])[C@H:9]([O:28][CH3:29])[CH2:10]3)=[O:27])[CH:17]=[CH:18][CH:19]=2)[N:24]=1

Participants

3

Reactant 1

HCID 68703262HCID 68703262, compound

Product 1

HCID 86607260HCID 86607260, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbamate (h) (110 mg, 0.27 mmol) was dissolved in dichloromethane/triluoroacetic acid (2 ml/2 ml). After 1 hour the mixture was evaporated to dryness and the residue triturated with ether. The residue was then redissolved in 10% methanol in dichloromethane (20 ml) and treated with macroporous triethylammonium methylpolystyrene carbonate resin (2.8 mmol/g; 2.7 g, Argonaut Technologies). After 1 hour the mixture was filtered and the resin washed several times alternately with 10% methanol in dichloromethane then methanol. The combined filtrate and washings were evaporated affording a white solid (80 mg, 95%).

Workup

  1. customAfter 1 hour the mixture was evaporated to dryness
  2. customthe residue triturated with ether
  3. dissolutionThe residue was then redissolved in 10% methanol in dichloromethane (20 ml)
  4. additiontreated with macroporous triethylammonium methylpolystyrene carbonate resin (2.8 mmol/g; 2.7 g, Argonaut Technologies)
  5. filtrationAfter 1 hour the mixture was filtered
  6. washthe resin washed several times alternately with 10% methanol in dichloromethane
  7. customThe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-7133dbfde7274a94bba51388b96a28e6
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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