1,2-Dichloroethane → HCID 11707403, compound

HRID 1786553Notes

Reaction equation

HRID 1786553 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([NH:11][C:12](=[O:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:8][NH:7]1)=[O:5])[CH3:2].[C:33]([C:37]1[CH:38]=[C:39]([CH:43]=[C:44]([C:48]([CH3:51])([CH3:50])[CH3:49])[C:45]=1[O:46][CH3:47])[C:40](O)=[O:41])([CH3:36])([CH3:35])[CH3:34].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([NH:11][C:12](=[O:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:8][N:7]1[C:40](=[O:41])[C:39]1[CH:43]=[C:44]([C:48]([CH3:49])([CH3:50])[CH3:51])[C:45]([O:46][CH3:47])=[C:37]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:38]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 22324252HCID 22324252, compoundHCID 57597573HCID 57597573, compound

Product 1

HCID 11707403HCID 11707403, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To the solution of (2S,4S)-4-[6,6-Bis-(4-fluoro-phenyl)-hexanoylamino]-pyrrolidine-2-carboxylic acid ethyl ester (32) (0.39 g, 0.88 mmol) in dry CH2Cl2 (20 ml) was added 3,5-di-tert-butyl-4-methoxy benzoic acid (0.23 g, 0.88 mmol). To the reaction was added EDC (0.34 g, 1.76 mmol) and DMAP (cat), and the reaction mixture stirred under nitrogen at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue was dissolved in ethyl acetate: water (10:1) (150 ml). The organic was washed with water (30 ml, 2×) and 10% NaOH (10 ml), dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using pet ether: EtOAc (1:1) to give 0.46 g of desired product.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate: water (10:1) (150 ml)
  3. washThe organic was washed with water (30 ml, 2×) and 10% NaOH (10 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-a777f1168cba4253ad0ab4561a06139a
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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