Trifluoroacetic acid → HCID 20719108, compound

HRID 1250782Notes

Reaction equation

HRID 1250782 reaction equation
C([O:5][C:6](=[O:21])[C@H:7]([CH2:17][CH:18]([CH3:20])[CH3:19])[NH:8][C:9]([C@@H:11]1[CH2:15][CH2:14][C:13](=[O:16])[O:12]1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:16]=[C:13]1[O:12][C@H:11]([C:9]([NH:8][C@H:7]([C:6]([OH:21])=[O:5])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:10])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20719109HCID 20719109, compound

Product 1

HCID 20719108HCID 20719108, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{[(S)-(5-Oxo-tetrahydrofuran-2-yl)carbonyl]}-L-leucine tertbutylester (800 mg, 2.67 mmols) in CH2Cl2 (3.0 ml) cooled at 0° C., was added freshly distilled anhydrous trifluoroacetic acid (0.5 ml). After a night at room temperature the solvent was evaporated at reduced pressure and the residue was dissolved in Et2O. By adding n-hexane the compound (2e) separated as a brown oil and was dried and decanted in high vacuum; 650 mg (100%); [a]D22=−7° (1, methanol); IR (CHCl3): 3413, 3036, 2957, 1787, 1725, 1678, 1526, 1172, 1191 cm−1; 1H-NMR (CDCl3): d 0.87 and 0.93 [two s, 6, CH2CH(CH3)2], 1.37-1.83 [m, 3, CH2CH(CH3)2], 2.06-2.73 (m, 4, ring CH2CH2), 4.30-4.63 (m, 1, ring CH), 4.67-4.92 (m, 1, aCH), 6.92 (d, 1, NH, J=8 Hz), 8.15 (s, 1, COOH). Calculated for C17H30N2O5.½ H2O (cyclohexylamine salt): C, 56.66; H, 8.89; N, 7.77. Found C, 57.00; H, 9.12; N 8.13%.

Workup

  1. customAfter a night at room temperature the solvent was evaporated at reduced pressure
  2. dissolutionthe residue was dissolved in Et2O
  3. additionBy adding n-hexane the compound (2e)
  4. customseparated as a brown oil
  5. customwas dried
  6. customdecanted in high vacuum

Sources & evidence

ORD record
ord-97b691f889d949b6a88feb6caa743cb2
Source dataset
uspto-grants-2002_01
Patent number
US06339160B1

Reaction notes

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