Triethylamine → HCID 86601670, compound

HRID 269601Notes

Reaction equation

HRID 269601 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]([OH:31])[CH2:14][C@H:15]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:16]([O:18]C(C)(C)C)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(N(CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][C@H:13]1[CH2:14][C@H:15]([NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[C:16](=[O:18])[O:31]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 11396494tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate

Product 1

HCID 86601670HCID 86601670, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 7.60 g (17.3 mmol) of tert-butyl 5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoate (Org. Lett. (2001) 3, 20:3153-3155) in 516 ml of dichloromethane and 516 ml of trifluoroacetic acid is stirred at RT for 2 h. The solvent is evaporated. The remaining crude product is dissolved in 2.6 l of anhydrous methanol and, while stirring at 0° C., 6.3 g (28.8 mmol) of di-tert-butyl dicarbonate and 7.3 ml (52.43 mmol) of triethylamine are added. After 15 h, the reaction solution is evaporated and the residue is taken up in 1 l of ethyl acetate. After the phases have separated, the organic phase is extracted twice with a 5% citric acid solution, twice with water and once with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated. The crude product is purified by chromatography on silica gel with toluene/acetone (5/1). 4.92 g (78% of theory) of product are obtained.

Workup

  1. customThe solvent is evaporated
  2. dissolutionThe remaining crude product is dissolved in 2.6 l of anhydrous methanol
  3. customthe reaction solution is evaporated
  4. customAfter the phases have separated
  5. extractionthe organic phase is extracted twice with a 5% citric acid solution, twice with water and once with a saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product is purified by chromatography on silica gel with toluene/acetone (5/1)
  9. custom4.92 g (78% of theory) of product are obtained

Sources & evidence

ORD record
ord-b0bd0f64511d4a349a61d13929ee42f8
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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