1,2-Dichloroethane → HCID 66932288, compound

HRID 1958836Notes

Reaction equation

HRID 1958836 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:32])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[O:14][C:15]([C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH2:25][N:26]([CH2:28][CH3:29])[CH3:27])[CH:19]=3)=[N:16][N:17]=2)=[CH:8][C:7]=1[CH2:30][CH3:31].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:56](O)(=[O:59])[CH2:57][OH:58]>C1COCC1.CN(C=O)C>[CH2:30]([C:7]1[CH:8]=[C:9]([C:13]2[O:14][C:15]([C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH2:25][N:26]([CH2:28][CH3:29])[CH3:27])[CH:19]=3)=[N:16][N:17]=2)[CH:10]=[C:11]([CH3:12])[C:6]=1[O:5][CH2:4][C@@H:3]([OH:32])[CH2:2][NH:1][C:57](=[O:58])[CH2:56][OH:59])[CH3:31]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66932543HCID 66932543, compound

Product 1

HCID 66932288HCID 66932288, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5)-1-amino-3-[2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,3,4]oxadiazol-2-yl)-6-methyl-phenoxy]-propan-2-ol (214 mg, 488 μmol) in THF (5 mL), DIPEA (91 mg, 732 μmol), HOBt (66 mg, 488 μmol), EDC (94 mg, 488 μmol) and glycolic acid (37 mg, 488 μmol) is added. The mixture is stirred at rt for 1 h before DMF (2 mL) is added. Stirring is continued for 30 min. The mixture is concentrated in vacuo and then separated by prep. HPLC to give the title compound as a colourless oil (38 mg). LC-MS: tR=0.71 min; [M+1]+=497.23.

Workup

  1. additionis added
  2. concentrationThe mixture is concentrated in vacuo
  3. customseparated by prep

Sources & evidence

ORD record
ord-42ca4156039e4eb5978dfc6fa316b0f7
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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