Benzyl succinimido carbonate → HCID 58933435, compound

HRID 854322Notes

Reaction equation

HRID 854322 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:9]1)C1C=CC=CC=1.[CH2:25]([O:32][C:33]([O:35]N1C(=O)CCC1=O)=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C.CN(C=O)C.O.[OH-].[OH-].[Pd+2]>[CH2:25]([O:32][C:33]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:9]1)=[O:35])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 58933542HCID 58933542, compound

Product 1

HCID 58933435HCID 58933435, compound

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-benzyl-morpholin-2-ylmethyl)-4-hydroxy-benzamide (Step 1 above) (320 mg) was dissolved in ethanol (20 mL) and hydrogenated at 1 atm over 20% Pd(OH)2/C (250 mg) for 18 h. The catalyst was removed by filtration, washed with ethanol, and the filtrate evaporated, to give a solid. A portion (21 mg) of this material was dissolved in DMF (0.5 mL) and N-(benzyloxycarbonyloxy)succinimide (27 mg) was added. The reaction mixture was stirred for 10 min, one drop of water was added and the solution was purified by preparative reverse phase HPLC to give the 2-[(4-Hydroxy-benzoylamino)-methyl]-morpholine4-carboxylic acid benzyl ester compound.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol
  3. customthe filtrate evaporated
  4. customto give a solid
  5. customthe solution was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-034737bb727a46e69b1ed57adb18f591
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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