Potassium Sodium Tartrate → HCID 178456183, compound

HRID 2204305Notes

Reaction equation

HRID 2204305 reaction equation
C[Al](C)C.C([O:7][C:8]([C:10]1[CH:14]=[CH:13][N:12]([CH:15]([CH3:17])[CH3:16])[C:11]=1[CH:18]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1)=O)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH:18]2[C:11]3[N:12]([CH:15]([CH3:17])[CH3:16])[CH:13]=[CH:14][C:10]=3[C:8](=[O:7])[N:19]2[C@H:20]2[CH2:21][CH2:22][C@H:23]([OH:26])[CH2:24][CH2:25]2)=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 16682925TrimethylaluminumHCID 178469220HCID 178469220, compound

Product 1

HCID 178456183HCID 178456183, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A solution of trimethylaluminium (2M in toluene) [75-24-1] (16.75 mmol) was added to a solution of 2-[(4-chloro-phenyl)-(trans-4-hydroxy-cyclohexylamino)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step F2) (5.58 mmol) in toluene (25 mL) and the mixture was stirred at 75° C. for 25 h. The mixture was cooled to rt, poured onto a stirring ice-cold solution of saturated Rochelle's salt and then diluted with EtOAc. The phases were separated. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a beige solid. tR: 3.99 min (HPLC 1); ESI-MS: tR=0.97 min, [M+H]+ 373/375 (LC-MS 1); TLC: Rf=0.27 (EtOAc).

Workup

  1. temperatureThe mixture was cooled to rt
  2. customThe phases were separated
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-6046b9659eea427ba01469d1decb5acc
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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