Sodium Carbonate → HCID 178485746, compound

HRID 1439712Notes

Reaction equation

HRID 1439712 reaction equation
[CH3:1][NH:2][C@H:3]([C:10]([OH:12])=[O:11])[CH2:4][C:5]1[N:9]=[CH:8][NH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:19]([O:26][C:27]([N:29]1[C:33](=[O:34])[CH2:32][CH2:31][C@H:30]1[C:35]([OH:37])=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.O1CCOCC1>[CH2:19]([O:26][C:27]([N:29]1[C:33](=[O:34])[CH2:32][CH2:31][C@H:30]1[C:35]([N:2]([CH3:1])[C@H:3]([C:10]([OH:12])=[O:11])[CH2:4][C:5]1[N:9]=[CH:8][NH:7][CH:6]=1)=[O:37])=[O:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylateHCID 178484878HCID 178484878, compound

Product 1

HCID 178485746HCID 178485746, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Nα -Methyl-L-histidine (428 mg) and sodium carbonate (288 mg) was dissolved in water (5 ml) and the solution adjusted to pH 8.5. Benzyloxycarbonyl-L-pyroglutamic acid N-hydroxsuccinimido ester (933 mg) in dioxane (5 ml) was added and the solution stirred for 15 hrs at 22°. The solution was evaporated and the residue chromatographed on a silica gel column (15 × 330 mm) using isopropanol-ethyl acetate - acetic acid - water (3 : 1 : 1 : 1) as eluant to give, after evaporation of the appropriate fraction, the product (615 mg) as a white solid m.p. 192°-195° RF 3A 0.21 RF 3B 0.69 [α]D22 - 1.3° (c = 1, dimethylformamide)

Workup

  1. customThe solution was evaporated
  2. customthe residue chromatographed on a silica gel column (15 × 330 mm)
  3. customto give
  4. customafter evaporation of the appropriate fraction

Sources & evidence

ORD record
ord-f29ec14db2d1430793af42ed948beeb5
Source dataset
uspto-grants-1977_11
Patent number
US04060603

Reaction notes

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