Trifluoroacetic acid → 3-{[5-(3-Amino-propylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-phenyl-propionic acid trifluoroacetic acid salt

HRID 1061717Notes

Reaction equation

HRID 1061717 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][CH:8]([NH:15][C:16]([C:18]1[S:19][C:20]([C:23](=[O:36])[NH:24][CH2:25][CH2:26][CH2:27][NH:28]C(OC(C)(C)C)=O)=[CH:21][CH:22]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>ClCCl>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[NH2:28][CH2:27][CH2:26][CH2:25][NH:24][C:23]([C:20]1[S:19][C:18]([C:16]([NH:15][CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:7][C:6]([OH:37])=[O:5])=[O:17])=[CH:22][CH:21]=1)=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 540767673-{[5-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-phenyl-propionic Acid Tert-butyl Ester

Product 1

HCID 98268363-{[5-(3-Amino-propylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-phenyl-propionic acid trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With continued reference to Scheme G, preparation of compound VII was carried out using the procedure described for compound III. Compound VI: 3-{[5-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-phenyl-propionic acid tert-butyl ester (200 mg, 0.704 mmol) was dissolved in 4.0 ml of anhydrous dichloromethane and 4.0 ml of anhydrous TFA. This reaction mixture was left stirring over night at room temperature. The solvents were evaporated under reduced pressure and the resulting residue was dissolved in anhydrous methanol (smallest amount possible). Diethyl ether was then added to precipitate the desired product, the supernatant was discarded and the solid washed with ether again then dried under reduced pressure to give 156 mg of the desired product as a white powder (Compound VII). 1H NMR (400 Mhz, DMSO-d6) 1.75 (m, 2H), 2.9 (m, 4H), 3.3 (m, 2H), 7.2-7.4 (m, 5H), 7.4 7.9 (bs, 3H), 7.65 (d, 1H), 7.8 (d, 1H), 8.75 (t, 1H), 9.05 (d, 1H).

Workup

  1. waitThis reaction mixture was left
  2. customThe solvents were evaporated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in anhydrous methanol (smallest amount possible)
  4. additionDiethyl ether was then added
  5. customto precipitate the desired product
  6. washthe solid washed with ether again
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-5f9ed9692ba44cf9980aac9e3393cc59
Source dataset
uspto-grants-2005_11
Patent number
US06960594B2

Reaction notes

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