Trifluoroacetic acid → HCID 86607258, compound

HRID 1437339Notes

Reaction equation

HRID 1437339 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][C@@H:11]([C:14](=[O:28])[NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[C:23]([C:26]#[N:27])[CH:22]=[CH:21]3)[CH2:10][C@@H:9]1[OH:29])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C: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]([OH:29])[CH2:10]3)=[O:28])[CH:17]=[CH:18][CH:19]=2)[N:24]=1)#[N:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68701274HCID 68701274, compound

Product 1

HCID 86607258HCID 86607258, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of carbamate (i) (2.4 g, 6 mmol) in dichloromethane (50 mL) was treated with trifluoroacetic acid (10 mL). After 18 hours the mixture was evaporated and partitioned between saturated aqueous sodium bicarbonate solution and 20% methanol/dichloromethane. The aqueous phase was twice more extracted and the combined extracts dried and evaporated giving a solid. This was triturated with ether/ethyl acetate (1/1) and filtered, washing with ether, to afford a light brown solid (1.25 g, 61%).

Workup

  1. customAfter 18 hours the mixture was evaporated
  2. custompartitioned between saturated aqueous sodium bicarbonate solution and 20% methanol/dichloromethane
  3. extractionThe aqueous phase was twice more extracted
  4. customthe combined extracts dried
  5. customevaporated
  6. customgiving a solid
  7. customThis was triturated with ether/ethyl acetate (1/1)
  8. filtrationfiltered
  9. washwashing with ether

Sources & evidence

ORD record
ord-5976968c62d7430791afc66ba4fa65fd
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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