Diisopropylethylamine → HCID 57187888, compound

HRID 1272558Notes

Reaction equation

HRID 1272558 reaction equation
[CH2:1]([NH:5][C:6](=[O:14])[CH:7](CCCCO)Cl)[CH2:2][CH2:3][CH3:4].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]2[C@H:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C@@H:26]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[CH2:25][NH:24]2)=[CH:19][CH:18]=1.C(O)(=O)[C@H:43]([C:45]1[CH:50]=[CH:49]C=CC=1)[OH:44].COC1C=CC([C@H]2[C@H](C(OCC)=O)[C@@H](C3C=CC4OCOC=4C=3)CN2)=CC=1.C(N(CC)C(C)C)(C)C>O.CS(C)=O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]2[C@H:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C@@H:26]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[CH2:25][N:24]2[CH2:7][C:6]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:49][CH2:50][CH2:45][CH2:43][OH:44])=[O:14])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 10926733220585-01-3HCID 22322998HCID 22322998, compoundHCID 131726349195708-14-6

Product 1

HCID 57187888HCID 57187888, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To 1.52 g (6.85 mmol) of the compound of Example 547B was added 2.75 g (7.44 mmol) of the ethyl (2S,3R,4S)-2-(4-Methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate (prepared by neutralization of the compound of Example 501G), 10 mL of DMSO, and 2 mL of N,N-diisopropylethylamine. The solution was stirred at ambient temperature for 22 h, then poured into 100 mL of water and extracted with diethyl ether (3×25 mL). The combined ether layers were washed with water (1×25 mL), 4% (v/v) H3PO4 (1×25 mL), saturated aqueous NaHCO3 solution (1×25 mL), and brine (1×25 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via silica gel chromatography, eluting with 98:2 diethyl ether: methanol to give 3.0 g (79%) of a colorless oil.

Workup

  1. extractionextracted with diethyl ether (3×25 mL)
  2. washThe combined ether layers were washed with water (1×25 mL), 4% (v/v) H3PO4 (1×25 mL), saturated aqueous NaHCO3 solution (1×25 mL), and brine (1×25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThis was purified via silica gel chromatography
  7. washeluting with 98:2 diethyl ether

Sources & evidence

ORD record
ord-7f48d8118ed9434186089dceda9eea52
Source dataset
uspto-grants-2007_04
Patent number
US07208517B1

Reaction notes

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