Sulfuric Acid → HCID 57551904, compound

HRID 1258488Notes

Reaction equation

HRID 1258488 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-f8d6b283398d4a3ea2a37d5b8a1e7640
Source dataset
uspto-grants-2013_06
Patent number
US08466158B2

Reaction notes

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