Triethylamine → HCID 11719511, compound

HRID 602340Notes

Reaction equation

HRID 602340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[O:30]=[C:31]1[CH2:36][O:35][CH2:34][CH2:33][N:32]1[C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]([C@H:46]2[CH2:50][C@@H:49]([OH:51])[CH2:48][NH:47]2)=[O:45])=[CH:39][CH:38]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:30]=[C:31]1[CH2:36][O:35][CH2:34][CH2:33][N:32]1[C:37]1[CH:38]=[CH:39][C:40]([NH:43][C:44]([C@H:46]2[CH2:50][C@@H:49]([OH:51])[CH2:48][N:47]2[C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:45])=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 58691270HCID 58691270, compound

Product 1

HCID 11719511HCID 11719511, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.25 g (1.46 mmol) of 4-chlorophenylacetic acid and 0.36 g (1.46 mmol) of ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) are added successively at room temperature to a solution of 0.5 g (1.46 mmol) of N-[4-(3-oxomorpholin-4-yl)phenyl]-(2R,4R)-4-hydroxypyrrolidine-2-carboxamide (Example 7.2) and 0.2 ml of triethylamine in 20 ml of toluene. The resultant reaction mixture is subsequently left to stir at room temperature for 12 hours, then washed successively with 10 ml of 1N hydrochloric acid and 10 ml of saturated sodium hydrogencarbonate solution, and the organic phase is dried over sodium sulfate. After the solvent has been stripped off, the crude product is purified by preparative HPLC, giving 0.31 g (46.4%) of N-[4-(3-oxomorpholin-4-yl)phenyl]-(2R,4R)-1-[2-(4-chlorophenyl)acetyl]-4-hydroxypyrrolidine-2-carboxamide as a white powder, ESI 458, m.p. 141°.

Workup

  1. customThe resultant reaction mixture
  2. waitis subsequently left
  3. washwashed successively with 10 ml of 1N hydrochloric acid and 10 ml of saturated sodium hydrogencarbonate solution
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-957efe6adb3e4c259e52e0be6320fbe2
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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