Dimethylformamide → HCID 86750060, compound

HRID 1080882Notes

Reaction equation

HRID 1080882 reaction equation
Cl.[OH:2][C:3]1[C:36]([CH3:37])=[CH:35][C:6]([C:7]([NH:9][CH:10]2[CH2:14][NH:13][CH2:12][CH:11]2[O:15][C:16](=[O:34])[C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:33])[C:24]3[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=3[OH:32])=[CH:19][CH:18]=2)=[O:8])=[CH:5][C:4]=1[CH3:38].C([N:41]([CH2:44]C)CC)C.C[N:47](C)C=O>>[NH2:47][C:44](=[NH:41])[N:13]1[CH2:14][CH:10]([NH:9][C:7](=[O:8])[C:6]2[CH:35]=[C:36]([CH3:37])[C:3]([OH:2])=[C:4]([CH3:38])[CH:5]=2)[CH:11]([O:15][C:16](=[O:34])[C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:33])[C:24]3[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=3[OH:32])=[CH:19][CH:18]=2)[CH2:12]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 86750061HCID 86750061, compound

Product 1

HCID 86750060HCID 86750060, compound

Procedure

A mixture of 14 mg of 4-(2-hydroxy-5-methoxy-benzoyl)-benzoic acid (3RS,4SR)-4-(4-hydroxy-3,5-dimethylbenzoylamino)-pyrrolidin-3-yl ester hydrochloride (Example 70), 0.01 ml of triethylamine and 37 mg of formamidinesulphonic acid in 2 ml of dimethylformamide was stirred at room temperature for 6 days. The solvent was evaporated under reduced pressure and the residue was taken up in water, sonicated and filtered. After drying under reduced pressure there were obtained 8 mg of 4-(2-hydroxy-5-methoxy-benzoyl)-benzoic acid (3RS, 4SR)-1-(amino-iminomethyl)-4-(4-hydroxy-3,5-dimethylbenzoyl amino)-pyrrolidin-3-yl ester as a yellow powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customsonicated
  3. filtrationfiltered
  4. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-4e2bc029922849009fc57022db661fe4
Source dataset
uspto-grants-1996_12
Patent number
US05583222

Reaction notes

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