4-Acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid → HCID 70248916, compound

HRID 2268805Notes

Reaction equation

HRID 2268805 reaction equation
Cl.C[O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[CH:10][CH:9]=1)[NH2:6].[CH3:25][C:26]1[C:30]([C:31](=[O:33])[CH3:32])=[C:29]([CH3:34])[NH:28][C:27]=1[C:35](O)=[O:36]>>[Cl:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C@@H:5]([C:4]([OH:3])=[O:24])[NH:6][C:35]([C:27]2[NH:28][C:29]([CH3:34])=[C:30]([C:31](=[O:33])[CH3:32])[C:26]=2[CH3:25])=[O:36])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 2232774-Acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acidHCID 69806827HCID 69806827, compound

Product 1

HCID 70248916HCID 70248916, compound

Procedure

from O-(2,6-dichlorobenzyl)-L-tyrosine methyl ester hydrochloride and 3,5-dimethyl-4-acetylpyrrole-2-carboxylic acid. Freeze drying afforded the title compound as a light cream amorphous solid (550 mg). δH (DMSO-d6) 11.56, (1H, s), 7.61 (1H, d, J 7.8 Hz), 7.51 (2H, d, J 8.0 Hz), 7.41 (1H, t, J 8.0 Hz), 7.21 (2H, d, J 85 Hz), 6.96 (2H, d, J 8.5 Hz), 5.16 (2H, s), 4.69-4.55 (1H, m), 3.12 (1H, dd, J 13.7, 4.7 Hz), 2.99 (1H, dd, J 13.7, 9.1 Hz), 2.43 (3H, s), 2.38 (3H, s), 2.31 (3H, s); m/z (ESI, 60V) 503 (MH+).

Workup

  1. customFreeze drying

Sources & evidence

ORD record
ord-c5555614bc8e4f74b912bcde373899d0
Source dataset
uspto-grants-2001_12
Patent number
US06329372B1

Reaction notes

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