4-phenyl-1H-pyrrole-3-carboxylic Acid → HCID 69818559, compound

HRID 2417444Notes

Reaction equation

HRID 2417444 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C@H:7]([N:10]([CH2:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[OH:20])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][OH:9])=[CH:4][CH:3]=1.[C:30]1([C:36]2[C:37]([C:41](O)=[O:42])=[CH:38][NH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[Cl:27][C:23]1[CH:22]=[C:21]([C@@H:19]([OH:20])[CH2:18][N:10]([C@@H:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:41]([C:37]3[C:36]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:40][NH:39][CH:38]=3)=[O:42])=[CH:29][CH:28]=2)[CH2:8][OH:9])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])[CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 15193794-phenyl-1H-pyrrole-3-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69817835HCID 69817835, compound

Product 1

HCID 69818559HCID 69818559, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl N-[(1S)-1-(4-aminobenzyl)-2-hydoxyethyl]-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]carbamate (120 mg) in N,N-dimethylformamide (2.0 ml) was added successively 4-phenyl-1H-pyrrole-3-carboxylic acid (64.0 mg) and 1-hydroxybenzotriazole hydrate (46.2 mg). To the mixture was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (65.6 mg) at room temperature and the mixture was stirred overnight. The mixture was diluted with ethyl acetate (20 ml) and washed with water (20 ml×2), a saturated aqueous sodium hydrogencarbonate solution (20 ml×1) and brine (20 ml×1) successively. The organic solution was dried over magnesium sulfate, filtered, and evaporated to give a yellow solid. The crude product was purified by a recycling preparative high pressure liquid chromatography equipped with a gel permeation chromatography column (eluent: chloroform) to give tert-butyl N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-N-[(1S)-2-hydroxy-1-[4-[[(4-phenyl-1H-pyrrol-3-yl)carbonyl]amino]benzyl]ethyl]carbamate (16 mg) as a yellow foam.

Workup

  1. washwashed with water (20 ml×2)
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a yellow solid
  6. customThe crude product was purified by a recycling preparative high pressure liquid chromatography
  7. customequipped with a gel permeation chromatography column (eluent: chloroform)

Sources & evidence

ORD record
ord-e52f317c8dec4f098f7e8268b3e9f0c3
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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