1-Methyl-2-pyrrolecarboxylic acid → HCID 69818904, compound

HRID 2417442Notes

Reaction equation

HRID 2417442 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C@H:7]([N:10]([CH2:18][C@H:19]([OH:28])[CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][OH:9])=[CH:4][CH:3]=1.[CH3:31][N:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](O)=[O:38].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[OH:9][CH2:8][C@@H:7]([N:10]([CH2:18][C@H:19]([OH:28])[CH2:20][O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:37]([C:33]2[N:32]([CH3:31])[CH:36]=[CH:35][CH:34]=2)=[O:38])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69817650HCID 69817650, compound

Product 1

HCID 69818904HCID 69818904, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl N-[(1S)-1-(4-aminobenzyl)-2-hydroxyethyl]-N-[(2S)-2-hydroxy-3-phenoxypropyl]carbamate (200 mg) in N,N-dimethylformamide (2.0 ml) was added successively 1-methyl-1H-pyrrole-2-caroxylic acid (72.1 mg) and 1-hydroxybenzotriazole hydrate (77.9 mg). To the mixture was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (110 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-[(1S)-2-hydroxy-1-[4-[[(1-methyl-1H-pyrrol-2-yl)carbonyl]amino]benzyl]ethyl]-N-[(2S)-2-hydroxy-3-phenoxypropyl]carbamate (163 mg) as a white 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-711cd4543b8b402280b802683bd1719d
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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