Triethylamine → HCID 15673238, compound

HRID 1196459Notes

Reaction equation

HRID 1196459 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C@H:10]1[O:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[SH:20][C@@H:21]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>C(O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C@@H:10]([OH:12])[CH2:11][S:20][C@@H:21]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11054718HCID 11054718, compoundHCID 15673225Ethyl (S)-2-Mercapto-4-methylpentanoate

Product 1

HCID 15673238HCID 15673238, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.85 g (10.6 mmole) of (2R,3S) 3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane, 1.86 g (10.6 mmole) of ethyl (S)-2-mercapto-4-methylpentanoate, and 1.48 ml (1.07 g. 10.6 mmole) of triethylamine in 40 ml of absolute ethanol was stirred overnight at room temperature under N2. The solution was concentrated in vacuo. The residue was taken up in CH2Cl2 and washed with 0.2N HCl followed by saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered, and rotary evaporated. The residual oil was chromatographed on a column of silica gel (57×4.3 cm) packed in hexane (elution with 7:1 and then 4:1 hexane ethyl acetate). Concentration of clean product fractions yielded 4.02 g (85%) of an oil, [α]20D -63.9°, TLC in 4:1 hexane-ethyl acetate. Mass spectrum and 200 MHz NMR confirmed the structure.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washwashed with 0.2N HCl
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customThe residual oil was chromatographed on a column of silica gel (57×4.3 cm)
  6. washelution with 7:1

Sources & evidence

ORD record
ord-a34b25e38acd438dab7a6a2a226a1bdd
Source dataset
uspto-grants-1992_05
Patent number
US05114925

Reaction notes

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