Sodium Carbonate → HCID 67619423, compound

HRID 2293345Notes

Reaction equation

HRID 2293345 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>C(#N)C>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([N:16]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 62576Benzyl bromoacetateHCID 86751513HCID 86751513, compound

Product 1

HCID 67619423HCID 67619423, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
22 °C

Procedure

A solution of L-proline-L-isoleucine benzylamide (10.22 g, 32.20 mmol), and sodium carbonate (6.824 g, 64.39 mmol, 2.0 eq), in acetonitrile (150 mL) was warmed to reflux until homogeneous, cooled to 22° C., and treated with benzyl 2-bromoacetate (14.75 g, 64.39 mmol, 2.0 eq). The flask was returned to the oil bath and warmed to reflux until TLC indicated the reaction was complete. The heterogeneous solution was filtered, concentrated to a residue, taken up in ethyl acetate (400 mL), and washed with satd aq NaHCO3 (2×50 mL). The solution was dried (MgSO4), concentrated to a residue, and purified by flash chromatography (20% ethyl acetate in hexane) to provide 14.80 g (99%) of L-isoleucine, N-[1-(2-benzyloxy-2-oxoethyl)-L-prolyl] benzylamide as a colorless oil.

Workup

  1. temperatureto reflux until homogeneous,
  2. temperaturewarmed
  3. temperatureto reflux until TLC
  4. filtrationThe heterogeneous solution was filtered
  5. concentrationconcentrated to a residue
  6. washwashed with satd aq NaHCO3 (2×50 mL)
  7. dry with materialThe solution was dried (MgSO4)
  8. concentrationconcentrated to a residue
  9. custompurified by flash chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-abf83c660c81421ea253f5be9d7a2e07
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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