Triethylamine → 8-[3-(tert-Butoxycarbonyl-methyl-amino)-pyrrolidine-1-sulfonyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate

HRID 1970037Notes

Reaction equation

HRID 1970037 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:34])[CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[NH:23][C:22](=[O:27])[C:21]4[NH:28][CH:29]=[C:30]([C:31]([OH:33])=[O:32])[C:20]=4[C:19]=3[CH:18]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OS(OCCC)(=O)=O)CC>>[C:1]([O:5][C:6]([N:8]([CH3:34])[CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[NH:23][C:22](=[O:27])[C:21]4[NH:28][CH:29]=[CH:30][C:20]=4[C:19]=3[CH:18]=2)(=[O:15])=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:30]([C:31]([O-:33])=[O:32])[CH2:20][CH3:19]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 69015Sulfuric acid, dipropyl esterHCID 575759848-[3-(tert-butoxycarbonyl-methyl-amino)-pyrrolidine-1-sulfonyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 866275358-[3-(tert-Butoxycarbonyl-methyl-amino)-pyrrolidine-1-sulfonyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate

Procedure

This compound was prepared according to general method of esterification C from 294 mg (0.6 mmol) of 8-[3-(tert-butoxycarbonyl-methyl-amino)-pyrrolidine-1-sulfonyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid, 836 μL (6 mmol) of triethylamine and 492 μL (3 mmol) of di-n-propylsulfate to give, after purification by chromatography on silica (eluent dichloromethane/methanol 98/2), 155 mg (50%) of 8-[3-(tert-butoxycarbonyl-methyl-amino)-pyrrolidine-1-sulfonyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate in the form of a brown solid.

Workup

  1. customThis compound was prepared
  2. customto give
  3. customafter purification by chromatography on silica (eluent dichloromethane/methanol 98/2), 155 mg (50%) of 8-[3-(tert-butoxycarbonyl-methyl-amino)-pyrrolidine-1-sulfonyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate in the form of a brown solid

Sources & evidence

ORD record
ord-82b348d89ef8400e96183aa3dbef94de
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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