Trifluoroacetic acid → HCID 67138785, compound

HRID 1592048Notes

Reaction equation

HRID 1592048 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][C:13]([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:12][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:11]=[CH:12][C:13]([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:14][CH:15]=1)[C:33]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67138412HCID 67138412, compound

Product 1

HCID 67138785HCID 67138785, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title A compond, ((S)-2-(4-[5-{4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-1-pentylcarbamoyl-ethyl)-carbamic acid t-butyl ester (64 mg, 0.108 mmol) in CH2Cl2 (1 mL) is treated with TFA (1 mL). After 20 min, the solvent is evaporated under stream of nitrogen. The residue is partitioned between EtOAc and saturated aqueous NaHCO3, and the organic solution is washed with brine, dried over anhydrous MgSO4, filtered and concentrated to yield (S)-2-amino-3-{4-[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. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e27c2836f79d474ea1d6f63f5e01f851
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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