Triethylamine → Carbonic Acid 2,5-Dioxopyrrolidin-1-yl (S)-Tetrahydrofuran-3-yl Ester

HRID 1372185Notes

Reaction equation

HRID 1372185 reaction equation
C1C(=O)N([O:8][C:9]([O:11][N:12]2[C:17](=[O:18])[CH2:16][CH2:15][C:13]2=[O:14])=[O:10])C(=O)C1.CCN(CC)CC.[CH3:26][CH2:27][O:28][C:29]([CH3:31])=O>CC#N>[O:28]1[CH2:29][CH2:31][C@H:26]([O:8][C:9](=[O:10])[O:11][N:12]2[C:13](=[O:14])[CH2:15][CH2:16][C:17]2=[O:18])[CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 676246Di(succinimido) carbonate

Product 1

HCID 11229944Carbonic Acid 2,5-Dioxopyrrolidin-1-yl (S)-Tetrahydrofuran-3-yl EsterYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 21 (250 mg, 2.84 mmol), N,N′-disuccinimidyl carbonate (799 mg, 3.12 mmol), and Et3N (431 mg, 4.27 mmol) in CH3CN (5 mL) were stirred for 12 hours at room temperature. Then the reaction mixture was diluted with EtOAc (20 mL), washed with brine, then concentrated under reduced pressure to obtain compound 22 (595 mg, 92%) as a solid. M.P.: 97–99° C.

Workup

  1. washwashed with brine
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee2597bcd3de481a9ba03e1852e19593
Source dataset
uspto-grants-2007_01
Patent number
US07157489B2

Reaction notes

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