Benzoic Acid → HCID 53988865, compound

HRID 1266460Notes

Reaction equation

HRID 1266460 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C1C=CC=CC=1.C(Cl)(=O)C(Cl)=O>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:9][N:8]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 7412Benzoyl chlorideHCID 65578Oxalyl chlorideHCID 539414194-(4-Nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Product 1

HCID 53988865HCID 53988865, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A stirred solution of 4-(4-nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (7.5 g, Reference Example 4) in methylene chloride (100 ml), at 23° C., was treated dropwise with triethylamine (5.8 ml). After stirring for 15 minutes the mixture was treated dropwise with a solution of benzoyl chloride [prepared in a separate vessel by treating a stirred solution of benzoic acid (5 g) in methylene chloride (15 ml), at 23° C., with oxalyl chloride (5 ml) and after stirring for 2 hours evaporating the reaction mixture] in methylene chloride (3.5 ml). The resulting dark brown mixture was stirred for 1.5 hours at 23° C. then filtered. The filtrate was successively washed with water (100 ml), then twice with hydrochloric acid (100 ml, 1N), then with brine (100 ml), then water (100 ml), then dried over magnesium sulphate and then evaporated (40° C. and 2.7 kPa) affording the title compound (10 g) as a viscous oil. 1H-NMR [400 MHz, (CD3)2SO at 383° K.] δ 1.13 (t, J=7 Hz, 3H); 3.49 (m, 1H); 3.65 (m, 1H); 3.75 to 3.90 (m, 2H); 3.90 to 4.20 (m, 2H); 4.09 (m, 2H);7.40 to 7.65 (m, 5H); 7.66 (d, J=8.5 Hz, 2H); 8.19 (d, J=8.5 Hz, 2H). MS [DCI (reactant gas, ammonia)]: 369[M+H]+, 386[M+NH4]+.

Workup

  1. customprepared in a separate vessel
  2. customevaporating the reaction mixture] in methylene chloride (3.5 ml)
  3. stirringThe resulting dark brown mixture was stirred for 1.5 hours at 23° C.
  4. filtrationthen filtered
  5. washThe filtrate was successively washed with water (100 ml)
  6. dry with materialtwice with hydrochloric acid (100 ml, 1N), then with brine (100 ml), then water (100 ml), then dried over magnesium sulphate
  7. customevaporated (40° C. and 2.7 kPa)

Sources & evidence

ORD record
ord-c48ab0b67c204f9491d983c6aa2ef41c
Source dataset
uspto-grants-2003_04
Patent number
US06548533B2

Reaction notes

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