Trifluoroacetic acid → HCID 73603622, compound

HRID 1500312Notes

Reaction equation

HRID 1500312 reaction equation
[F:1][CH:2]([F:38])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:24](=[O:35])[CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[N:22][CH:23]=3)=[CH:14][CH:13]=2)[O:7]C1(C)C)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl.O.C1(C)C=CC=CC=1>[NH2:27][CH2:26][CH2:25][C:24]([C:21]1[N:22]=[CH:23][C:18]([C:15]2[CH:14]=[CH:13][C:12]([C@@H:8]([OH:7])[C@H:9]([NH:5][C:3](=[O:4])[CH:2]([F:38])[F:1])[CH2:10][F:11])=[CH:17][CH:16]=2)=[CH:19][CH:20]=1)=[O:35]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713199HCID 86713199, compound

Product 1

HCID 73603622HCID 73603622, compoundYield 62.7%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product of step 3, Example 28 (554 mg, 1 mmol) in methylene chloride (20 ml) at 0° C. is treated with trifluoroacetic acid (10 ml) and allowed to warm to room temperature. After 30 minutes, water (3 drops) is added. The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is then diluted with toluene and evaporated. The material is purified by HPLC (Gemini NX C18MP A=0.1% trifluoroacetic acid in water MP B=0.1% trifluoroacetic acod in acetonitrile, Gradient 10% B to 50% in 10 min) to give title compound (248 mg): MS (ESI+) m/z 396.0 [M+H].

Workup

  1. customevaporated
  2. customThe material is purified by HPLC (Gemini NX C18MP A=0.1% trifluoroacetic acid in water MP B=0.1% trifluoroacetic acod in acetonitrile

Sources & evidence

ORD record
ord-6d056d1d7c124bfa948b382fd21b5c9f
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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