Toluene → (2S,4S)-4-Benzyloxycarbonylamino-1-{pentyl-[2'-(1-trityl-1H-tetrazol-5-yl) biphenyl-4-ylmethyl]carbamoyl}pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 425131Notes

Reaction equation

HRID 425131 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][NH:6]1)=[O:4].[CH2:21]([N:26]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:43]2[N:44]=[N:45][N:46](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:47]=2)=[CH:33][CH:32]=1)[C:27](Cl)=[O:28])[CH2:22][CH2:23][CH2:24][CH3:25].CCN([CH:73]([CH3:75])[CH3:74])C(C)C.[C:76]1([CH3:82])[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][N:6]1[C:27](=[O:28])[N:26]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:43]2[N:47]([C:82]([C:74]3[CH:73]=[CH:75][CH:9]=[CH:5][CH:3]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)[N:46]=[N:45][N:44]=2)=[CH:33][CH:32]=1)=[O:4]

Participants

5

Reactant 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 45072528(2S,4S)-4-Benzyloxycarbonylaminopyrrolidine-2-carboxylic Acid Methyl EsterHCID 59556775N-Pentyl-N-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]carbamoyl Chloride

Product 1

HCID 57648853(2S,4S)-4-Benzyloxycarbonylamino-1-{pentyl-[2'-(1-trityl-1H-tetrazol-5-yl) biphenyl-4-ylmethyl]carbamoyl}pyrrolidine-2-carboxylic Acid Methyl Ester

Conditions

Temperature
90 °C

Procedure

(2S,4S)-4-Benzyloxycarbonylaminopyrrolidine-2-carboxylic acid methyl ester (1.4 g, 5.1 mmol) and N-pentyl-N-[2′-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]carbamoyl chloride (1 equiv) were dissolved in toluene (100 mL). DIPEA (3 equiv) was added, and the solution was stirred at 90° C. for 16 hours. The solution was cooled, washed with water (100 mL), 1M HCl (100 mL) and saturated aqueous NaHCO3 (100 mL), then dried over Na2SO4. The solvent was evaporated to afford the title compound (3.93 g, 4.5 mmol).

Workup

  1. temperatureThe solution was cooled
  2. washwashed with water (100 mL), 1M HCl (100 mL) and saturated aqueous NaHCO3 (100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7045059b32aa4444940cb29a20691b2f
Source dataset
uspto-grants-2012_01
Patent number
US08106082B2

Reaction notes

Loading…