Triethylamine → HCID 68618081, compound

HRID 1158496Notes

Reaction equation

HRID 1158496 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18].[C:25]([O:29][C:30]([N:32]1[CH2:36][C@@H:35]([CH2:37][NH:38][CH:39]([CH3:41])[CH3:40])[C@H:34]([CH2:42][N:43]([S:48]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)(=[O:50])=[O:49])[CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:25]([O:29][C:30]([N:32]1[CH2:33][C@H:34]([CH2:42][N:43]([CH2:44][CH:45]([CH3:46])[CH3:47])[S:48]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)(=[O:50])=[O:49])[C@H:35]([CH2:37][N:38]([CH:39]([CH3:41])[CH3:40])[C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:14]([O:13][CH2:12][CH2:11][CH2:10][O:9][CH3:8])[CH:15]=2)[CH2:36]1)=[O:31])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 59512265HCID 59512265, compoundHCID 59512382HCID 59512382, compound

Product 1

HCID 68618081HCID 68618081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.48 mL, 3.43 mmol) followed by 3-(3-methoxy-propoxy)-4-methoxy-benzoic acid chloride (621 mg, 2.4 mmol) (prepared from 3-(3-methoxy-propoxy)-4-methoxy-benzoic acid and SOCl2 in CH2Cl2) is added to a solution of (3S*,4R*)-3-[(benzenesulfonyl-isobutyl-amino)-methyl]-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.07 g, 2.3 mmol) in CH2Cl2 (30 mL) and stirred at RT for 16 h. For workup a sat. solution of NaHCO3 is added and the mixture is extracted with ethyl acetate. The combined organic extracts are dried (Na2SO4), filtered and the solvent is evaporated. Purification of the crude product by flash chromatography on silica gel (eluent gradient: c-hexane/AcOEt 1:1 to 3:7) yields the title compound. TLC, Rf (c-hexane/AcOEt 3:7)=0.40; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 6.10 min.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent is evaporated
  5. customPurification of the crude product by flash chromatography on silica gel (eluent gradient: c-hexane/AcOEt 1:1 to 3:7)

Sources & evidence

ORD record
ord-dd2974493b354e3f8be0eb62d053ff57
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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