Triethylamine → HCID 57965703, compound

HRID 1673258Notes

Reaction equation

HRID 1673258 reaction equation
[CH3:1][O:2][C:3](=[O:35])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18](=[O:34])[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:12][CH:11]=1)OS(C)(=O)=O.[CH3:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40].O[C@H:44]1CC[NH:46][CH2:45]1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:35])[CH:4]([C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](=[O:34])[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[CH:12][CH:11]=1)[N:46]1[CH2:45][CH2:44][CH:37]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH2:36]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 72292924HCID 72292924, compound

Product 1

HCID 57965703HCID 57965703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-methanesulfonyloxy-acetic acid methyl ester (1.89 g, 3.75 mmol) and Et3N (1.46 g, 14.4 mmol) in CH2Cl2 (30 mL) was added (S)-3-hydroxypyrrolidine (0.67 g, 4.5 mmol). This mixture was stirred overnight at room temperature, then diluted with CH2Cl2 (50 mL), washed with saturated aqueous NaHCO3 solution, water and brine, dried with Na2SO4, filtered, and evaporated to obtain a yellow solid which was directly used in the next reaction without further purification. MS: calc'd 551 (MH+), exp 551 (MH+).

Workup

  1. washwashed with saturated aqueous NaHCO3 solution, water and brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto obtain a yellow solid which
  6. customwas directly used in the next reaction without further purification

Sources & evidence

ORD record
ord-542e27155f084edf906665be0f37bc01
Source dataset
uspto-grants-2011_08
Patent number
US07999000B2

Reaction notes

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