Trifluoroacetic acid → HCID 68908815, compound

HRID 1633892Notes

Reaction equation

HRID 1633892 reaction equation
C(C1CCC([N:11]([CH2:26][C:27]2[CH:44]=[CH:43][C:30]([C:31]([CH:33]([NH:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH:34]3[CH2:36][CH2:35]3)=[O:32])=[CH:29][CH:28]=2)[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[O:13])CC1)(C)(C)C.[C:45](O)([C:47](F)(F)F)=O>ClCCl>[C:27]([CH:45]1[CH2:47][CH2:17][CH:16]([CH:26]([NH:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=2)=[O:13])[C:27]2[CH:44]=[CH:43][C:30]([C:31]([CH:33]([NH:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH:34]3[CH2:35][CH2:36]3)=[O:32])=[CH:29][CH:28]=2)[CH2:15][CH2:20]1)([CH3:44])([CH3:28])[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67484036HCID 67484036, compound

Product 1

HCID 68908815HCID 68908815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above resin bound 3-({4-[1-(4-tert-butylcyclohexyl)-3-(4-trifluoromethoxyphenyl)-ureidomethyl]benzoyl}cyclopropylmethyl)aminopropionic acid (50 mg) was treated with 1 mL 5% TFA in dichloromethane for 1 hour at 25° C. The product was filtered off and the resin was washed with 1 mL dichloromethane. The combined extracts were concentrated in vacuo. The residue was dissolved in 50 μL DMSO+500 μL acetonitrile and purified by preparative HPLC using a Supelcosil ABZ+25 cm×10 mm 5μ column. The starting eluent composition was 5% acetonitrile in water changing over 30 min to 90% acetonitrile in water which was then kept constant for 5 min before going back to the starting composition over 10 min. The flow rate was kept constant at 8 mL/min collecting one fraction per minute. The process was monitored using an UV detector operating at 214 nm. The fractions containing the desired product were combined and evaporated in vacuo to afford the title compound.

Workup

  1. filtrationThe product was filtered off
  2. washthe resin was washed with 1 mL dichloromethane
  3. concentrationThe combined extracts were concentrated in vacuo
  4. dissolutionThe residue was dissolved in 50 μL DMSO+500 μL acetonitrile
  5. custompurified by preparative HPLC
  6. waitbefore going back to the starting composition over 10 min
  7. customcollecting one fraction per minute
  8. additionThe fractions containing the desired product
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-f5653c7776c94ad1a0cb83c19c650a7e
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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