Cyclohexanol → HCID 131731108, compound

HRID 1916029Notes

Reaction equation

HRID 1916029 reaction equation
CCN=C=NCCCN(C)C.Cl.[NH:13]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:14]([C:25]([OH:27])=[O:26])[C@@H:15]([CH3:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH:35]1(O)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[NH:13]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C@H:14]([C:25]([O:27][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:26])[C@@H:15]([CH3:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 7966CyclohexanolHCID 1549483L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 131731108HCID 131731108, compoundYield 95%

Procedure

EDC.HCl (7.5 g, 40 mmol) was added to a stirring solution of Boc-Thr(Bzl)-OH (10 g, 32 mmol), cyclohexanol (5.0 mL, 48 mmol), and OMAP (0.66 g, 5.3 mmol) in OCM (75 mL) at 0° C. The mixture was warmed to room temperature (rt) over 30 min and stirred additionally overnight. After removal of the solvent in vacuo, the residue was dissolved in AcOEt, washed successively with 5% citric acid (3×), 5% NaHCO3 (3×) and saturated NaCl (3×), dried over MgSO4, and concentrated in vacuo. The resulting oil was purified by silica gel column chromatography (AcOE:hexane 1:8) to yield oily Boc-Thr(Bzl)-OcHex (12 g, 30 mmol, 95%). 1H NMR (CDCl3 400 MHz) 67.34-7.25 (m, 5H), 5.28 (d, J=9.6 Hz, 1H), 4.83-4.77 (m, 1H), 4.54 (d, J=11.6 Hz, 1H), 4.38 (d, J=11.6 Hz, 1H), 4.26 (dd, J=2.2, 9.6 Hz, 1H), 4.15 (dq, J=2.2, 6.4 Hz, 1H), 1.84-1.81 (m, 1H), 1.78-1.62 (m, 4H), 1.56-1.46 (m, 1H), 1.45 (s, 9H), 1.44-1.28 (m, 4H), 1.26 (d, J=6.4 Hz, 3H).

Workup

  1. customAfter removal of the solvent in vacuo
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed successively with 5% citric acid (3×), 5% NaHCO3 (3×) and saturated NaCl (3×)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified by silica gel column chromatography (AcOE:hexane 1:8)

Sources & evidence

ORD record
ord-65dce46eba89495cb62af3f0af24a07f
Source dataset
uspto-grants-2013_12
Patent number
US08618049B2

Reaction notes

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