Water → HCID 68006824, compound

HRID 1475684Notes

Reaction equation

HRID 1475684 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2([C:19]([O:21]C(C)(C)C)=[O:20])[CH2:18][CH2:17]2)=[O:10])=[CH:4][CH:3]=1.O.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2([C:19]([OH:21])=[O:20])[CH2:18][CH2:17]2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68170308HCID 68170308, compound

Product 1

HCID 68006824HCID 68006824, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.60 g (14.1 mmol) of (+/−)-tert-butyl 1-(3-{[(4-chlorophenyl)(cyclopentyl)acetyl]amino}-benzyl)cyclopropanecarboxylate were dissolved in 41.8 ml of dichloromethane and, after addition of a drop of water, 10.9 ml of TFA were added at RT. The reaction mixture was stirred at RT for 1 h and then concentrated under reduced pressure. The residue was initially dried under high vacuum and then triturated with diisopropyl ether. The resulting solid was filtered off with suction and dried under high vacuum. This gave 4.52 g (77.8% of theory) of the target compound.

Workup

  1. additionwere added at RT
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was initially dried under high vacuum
  4. customtriturated with diisopropyl ether
  5. filtrationThe resulting solid was filtered off with suction
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-5583ef64923e4510bbae9da4d430abae
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

Loading…