Trifluoroacetic acid → HCID 67138311, compound

HRID 1591988Notes

Reaction equation

HRID 1591988 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:34](=[O:41])[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]2[CH2:21][C:20](=[O:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[S:18]2(=[O:33])=[O:32])[CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]2[CH2:21][C:20](=[O:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[S:18]2(=[O:32])=[O:33])[CH:11]=1)[C:34]([NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67139995HCID 67139995, compound

Product 1

HCID 67138311HCID 67138311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title F compound, ((S)-2-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-phenyl}-1-pentylcarbamoyl-ethyl)-carbamic acid t-butyl ester (77 mg, 0.127 mmol) in CH2Cl2 (1 mL) is added TFA (1 mL). After 30 min, the solvent is removed under stream of nitrogen. The residue is partitioned between EtOAc and saturated aqueous NaHCO3. The organic solution is washed with brine, dried over anhydrous MgSO4 and concentrated to yield (S)-2-amino-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-phenyl}-N-pentyl-propionamide as a clear oil: [M+1]+=503.

Workup

  1. customthe solvent is removed under stream of nitrogen
  2. customThe residue is partitioned between EtOAc and saturated aqueous NaHCO3
  3. washThe organic solution is washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1bfa2dfe5a9a4eb69175f46233329308
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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