1,2-Dichloroethane → HCID 58333550, compound

HRID 2066853Notes

Reaction equation

HRID 2066853 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][OH:29])=[CH:23][C:22]=3[F:30])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[C:31]([NH:38][C@H:39]([C:43](O)=[O:44])[CH:40]([CH3:42])[CH3:41])([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][O:29][C:43](=[O:44])[C@@H:39]([NH:38][C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH:40]([CH3:42])[CH3:41])=[CH:23][C:22]=3[F:30])[CH2:19][CH2:20]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 83693Boc-L-ValineHCID 58333373HCID 58333373, compound

Product 1

HCID 58333550HCID 58333550, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

10-1 (0.5 g, 1.19 mmol), Boc-L-valine (0.27 g, 1.28 mmol), DMAP (36 mg) and EDC(0.27 g) were combined in 10 mL of DCM and stirred at room temperature for 18 h. The mixture was concentrated and purified by flash LC(eluent: 0 to 40% EtOAc in hexane with 0.1% of triethylamine) to afford 42-1 as a colorless oil: LC-MS 525.2 (MH-Boc), tR=10.38 (Method 2). EC50: 928 nM.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash LC(eluent

Sources & evidence

ORD record
ord-3551a33b880747a5a31fab24e0fa37c4
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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