HCID 25167880, compound → HCID 178481167, compound

HRID 599485Notes

Reaction equation

HRID 599485 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16][CH:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[N:30]([CH3:31])[C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:19][CH2:18]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[NH2:35][C@H:36]([C:44]([OH:46])=[O:45])[CH2:37][CH2:38][CH2:39][NH:40][C:41](=[NH:43])[NH2:42]>CCO.O>[NH2:35][C@H:36]([C:44]([OH:46])=[O:45])[CH2:37][CH2:38][CH2:39][NH:40][C:41](=[NH:42])[NH2:43].[C:1]([C:5]1[CH:6]=[C:7]([S:16][CH:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[N:30]([CH3:31])[C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:19][CH2:18]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 25167880HCID 25167880, compoundHCID 178418600HCID 178418600, compound

Product 1

HCID 178481167HCID 178481167, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid (Ex. 4, 0.60 g, 1.18 mmol) in EtOH (2.4 mL) at room temperature was added a solution of L-arginine (0.20 g, 1.18 mmol) in water (2.4 mL). After 5 min of stirring, the mixture solidified and an additional 3 mL of EtOH was added to ensure a homogeneous solution. It was stirred at room temperature for 1 h and then concentrated under reduced pressure. The solid residue was triturated with EtOH (2.4 mL×2). The material was then taken up again in EtOH and stirred at room temperature overnight. The resulting solid was collected on filter paper and dried in vacuo to afford 0.48 g (60%) of the title compound as a white solid, mp 216-220° C. 1H-NMR (400 MHz, DMSO-d6): δ 7.98 (brs, 5H), 7.22 (s, 1H), 7.10 (s, 2H), 6.52 (s, 1H), 3.88 (s, 3H), 3.43-3.46 (m, 2H), 3.06-3.12 (m, 3H), 2.96-2.98 (m, 1H), 2.35 (t, 2H, J=11.0 Hz), 1.90-1.93 (m, 2H), 1.56-1.72 (m, 4H), 1.45-1.51 (m, 2H), 1.35 (s, 18H), 1.04-1.08 (m, 1H). HRMS (ESI) Calcd. for C31H50N6O7S2, 683.3260 ([M+H]+). Found: 683.3272. Anal. Calcd. for C31H50N6O7S2.2H2O: C, 51.79; H, 7.57; N, 11.69; S, 8.92. Found: C, 51.94; H, 7.47; N, 11.53; S, 8.85.

Workup

  1. stirringIt was stirred at room temperature for 1 h
  2. concentrationconcentrated under reduced pressure
  3. customThe solid residue was triturated with EtOH (2.4 mL×2)
  4. stirringstirred at room temperature overnight
  5. customThe resulting solid was collected
  6. filtrationon filter paper
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b4cd2bc30775411cab7f96d537c9acde
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

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