Trifluoroacetic acid → HCID 58622270, compound

HRID 2220704Notes

Reaction equation

HRID 2220704 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[C:32](Cl)=[O:33].C(N(CC)CC)C.C(O)(C(F)(F)F)=O>C(#N)C.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:14]([C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[C:32](=[O:33])[C:31]1[CH:35]=[CH:36][C:37]([O:38][CH3:39])=[C:29]([O:28][CH3:27])[CH:30]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 58622171HCID 58622171, compound

Product 1

HCID 58622270HCID 58622270, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Experimental condition analogous to Example 4, from 2-(S)-(biphenyl-3-ylaminomethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 1 g (2.84 mmol), 3,4-dimethoxy-benzoyl chloride 0.6 g (2.98 mmol), and triethylamine 0.43 g (4.26 mmol), and 25 mL of dichloromethane. After purification on silica using gradient of chloroform-ethylacetate (20-1 to 10-1) gave 1 g of white semi solid compound: LC-MSD, m/z for: C31H36N2O5 [M+H]: 517.6. LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 7 minutes: 5.093

Workup

  1. customAfter purification on silica using gradient of chloroform-ethylacetate (20-1 to 10-1)
  2. customgave 1 g of white semi solid compound

Sources & evidence

ORD record
ord-7e7d589e5710409194a713e06ea4f775
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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