Trifluoroacetic acid → HCID 45496562, compound

HRID 1672251Notes

Reaction equation

HRID 1672251 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][CH:6]([NH:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)=[O:16])[C:7]([O:9]C(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>ClC(Cl)C>[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][CH:6]([NH:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:21][CH:22]=1)=[O:16])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67333002HCID 67333002, compound

Product 1

HCID 45496562HCID 45496562, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-[(Biphenyl-4-carbonyl)-amino]-pentanedioic acid 1-tert-butyl ester 5-methyl ester (1.5 g, 3.8 mmol) was dissolved in dichloroethane (26 mL) and the mixture was added to TFA (13 mL). The mixture was stirred at room temperature for 4 hrs. TLC indicated the reaction was complete. Solvent was evaporated by rotovap. The solid obtained was washed with EtOAc and water. After drying, 2-[(Biphenyl-4-carbonyl)-amino]-pentanedioic acid 5-methyl ester was obtained in 87% yield (1.128 g). MS (ESI) m/z 342.

Workup

  1. customSolvent was evaporated by rotovap
  2. customThe solid obtained
  3. washwas washed with EtOAc and water
  4. customAfter drying

Sources & evidence

ORD record
ord-a9b9b19f7b54470395dfad39999f4003
Source dataset
uspto-grants-2011_08
Patent number
US07998965B2

Reaction notes

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