Sulfuric Acid → HCID 57551904, compound

HRID 218083Notes

Reaction equation

HRID 218083 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C@@H:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:15]([OH:17])=[O:16])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH:27](O)([CH3:29])[CH3:28]>>[CH:27]([O:16][C:15](=[O:17])[C@@H:14]([NH:13][C@@H:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:9]([F:12])([F:11])[F:10])[CH2:18][CH:19]([CH3:21])[CH3:20])([CH3:29])[CH3:28]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 57446946N-[(1S)-1-(4-Bromophenyl)-2,2,2-trifluoroethyl]-L-leucine

Product 1

HCID 57551904HCID 57551904, compoundYield 88%

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (S)-2-[(S)-1-(4-bromo-phenyl)-2,2,2-trifluoro-ethylamino]-4-methyl-pentanoic acid, prepared as shown in Li, C. S. et al Bioorg. Med. Chem. Lett. 2006, 16, 1985, (1.80 g, 4.9 mmol) in isopropyl alcohol (100 mL) was added concentrated sulphuric acid (2 mL). The resulting solution was heated at 80° C. for 4 hours. The reaction mixture was allowed to cool and was then concentrated in vacuo. The resulting oil was dispersed in CH2Cl2 (100 mL), washed with saturated NaHCO3 (2×50 mL), dried (MgSO4) and concentrated in vacuo to yield the title compound as a brown oil (1.77 g, 88%). MS [M+H] 412.

Workup

  1. temperatureto cool
  2. concentrationwas then concentrated in vacuo
  3. additionThe resulting oil was dispersed in CH2Cl2 (100 mL)
  4. washwashed with saturated NaHCO3 (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-944e6250413b401b8c95992d8d80b043
Source dataset
uspto-grants-2012_06
Patent number
US08198283B2

Reaction notes

Loading…