Hydrochloric Acid → HCID 70229222, compound

HRID 634995Notes

Reaction equation

HRID 634995 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][C:14]([OH:16])=[O:15])[C@H:10]([CH2:17][C:18]([OH:20])=[O:19])[CH2:9]1)C1C=CC=CC=1.[C:21]([O-:24])([O-])=O.[Na+].[Na+].ClC(OC[C:32]1[C:44]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][CH:33]=1)=O.Cl.C([OH:48])C>O.O1CCOCC1.C1(C)C=CC=CC=1.[Pd]>[C:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][C:14]([OH:16])=[O:15])[C@H:10]([CH2:17][C:18]([OH:20])=[O:19])[CH2:9]1)([O:24][CH2:21][CH:43]1[C:44]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:48]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 14261773Fluorenylmethyl chloroformateHCID 70229250HCID 70229250, compound

Product 1

HCID 70229222HCID 70229222, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

N-Benzyl-trans-3,4-bis-(Carboxymethyl)-Pyrrolidine is dissolved in ethanol, and a catalytic amount of 10% Pd/C is added. The suspension is shaken under 3 atm H2 overnight. The catalyst is filtered, the solvent removed and the residue and Na2CO3 (1.3 eq) are suspended in H2O/Dioxane (1:1) (0.1M). Fluorenylmethyl chloroformate (1.1 eq) in toluene is added dropwise. The temperature of the reaction is not allowed to rise above 25° C. during the addition. The mixture is stirred vigorously overnight, acidified to pH 3 with conc HCl, and extracted twice with ethyl acetate. The organic extract is washed with brine, dried with MgSO4, filtered and the solvent removed in vacuo. The product is purified by chromatography.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent removed
  3. additionto rise above 25° C. during the addition
  4. stirringThe mixture is stirred vigorously overnight
  5. extractionextracted twice with ethyl acetate
  6. extractionThe organic extract
  7. washis washed with brine
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customthe solvent removed in vacuo
  11. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-48750bb2f4304feea2fbb06373a6dac8
Source dataset
uspto-grants-2001_02
Patent number
US06184389B2

Reaction notes

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