Trifluoroacetic acid → HCID 86695504, compound

HRID 1487551Notes

Reaction equation

HRID 1487551 reaction equation
FC(F)(F)C(O)=O.[F:8][CH:9]([F:46])[C:10]([N:12]1[C@H:16]([CH2:17][F:18])[C@@H:15]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][C:28]([CH:31]([NH:33][C:34](=[O:43])[O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH3:32])=[N:29][CH:30]=3)=[CH:21][CH:20]=2)[O:14]C1(C)C)=[O:11]>C(Cl)Cl>[F:46][CH:9]([F:8])[C:10]([NH:12][C@H:16]([CH2:17][F:18])[C@@H:15]([C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:26]=[CH:27][C:28]([CH:31]([NH:33][C:34](=[O:43])[O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH3:32])=[N:29][CH:30]=2)=[CH:23][CH:24]=1)[OH:14])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695502HCID 86695502, compound

Product 1

HCID 86695504HCID 86695504, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.2 mL) is added to the product of step 2, Example 95A (1.05 g, 1.94 mmol) in CH2Cl2 (39 mL) at 0° C. After 30 minutes the ice bath is removed and the mixture stirred at room temperature for 8 hours. Saturated NaHCO3 (60 mL) is added and the mixture extracted with CH2Cl2 (40 mL). The combined organics are dried over MgSO4, filtered and evaporated to give the title product (850 mg): m/z: 501.19.

Workup

  1. customAfter 30 minutes the ice bath is removed
  2. additionSaturated NaHCO3 (60 mL) is added
  3. extractionthe mixture extracted with CH2Cl2 (40 mL)
  4. dry with materialThe combined organics are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-595f5de0b02a4d3c88fa9de079594761
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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