1,2-Dichloroethane → HCID 57733404, compound

HRID 1962411Notes

Reaction equation

HRID 1962411 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([OH:10])=O.ClCCCl.[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][C:26](=[O:37])[NH:27][C@H:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][CH3:30])[C:17]=1[C:18]([OH:20])=O.C(N(CC)CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[C:18](=[O:20])[O:37][C:26]([NH:27][C@H:28]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:29][CH3:30])=[C:25]2[C:8](=[O:10])[CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acidHCID 57733407HCID 57733407, compound

Product 1

HCID 57733404HCID 57733404, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 2-oxo-pyrrolidin-1-yl-acetic acid (1.56 g, 10.9 mmol) in 1,2-dichloroethane (40 ml) oxalyl chloride (0.95 ml, 10.9 mmol) and DMF (1 drop) were added with gas evolution observed. After stirring at r.t. for 1 hour, 2-fluoro-6-[((S)-1-phenyl-propylcarbamoyl)-methyl]-benzoic acid (1.56 g, 4.95 mmol), triethylamine (2.1 ml, 14.9 mmol) and DMAP (85 mg, 0.1 eq.) were added and stirred at r.t. overnight. It was partitioned between mixture of 0.2 M aq. HCl (100 ml) —brine (100 ml) and ethyl acetate (250 ml), washed with water and evaporated to give 1.89 g of crude title compound used in the next step without further purification.

Workup

  1. stirringstirred at r.t. overnight
  2. customIt was partitioned between mixture of 0.2 M aq. HCl (100 ml) —brine (100 ml) and ethyl acetate (250 ml)
  3. washwashed with water
  4. customevaporated

Sources & evidence

ORD record
ord-6b6f65b22e9543e5846f8886c4aca45d
Source dataset
uspto-grants-2013_04
Patent number
US08415373B2

Reaction notes

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