Trifluoroacetic acid → HCID 67138347, compound

HRID 1592059Notes

Reaction equation

HRID 1592059 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:33](=[O:40])[NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:20][C:19](=[O:21])[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[S:17]2(=[O:32])=[O:31])[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]([N:16]2[CH2:20][C:19](=[O:21])[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[S:17]2(=[O:31])=[O:32])[CH:11]=1)[C:33]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67139578HCID 67139578, compound

Product 1

HCID 67138347HCID 67138347, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title F compound, ((S)-2-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-1-pentylcarbamoyl-ethyl)-carbamic acid t-butyl ester (156 mg, 0.265 mmol) in CH2Cl2 (1 mL) is treated with TFA (1 mL). After 30 min, the solvent is evaporated 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-yl]-phenyl}-N-pentyl-propionamide as a white solid: [M+1]+=489.

Workup

  1. customthe solvent is evaporated 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-d454f6235f8f40afb364042a54751e37
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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