1,2-Dichloroethane → HCID 66787107, compound

HRID 2367002Notes

Reaction equation

HRID 2367002 reaction equation
[OH:1][C:2]1([C:12]2[S:13][CH:14]=[C:15]([C:17]([OH:19])=O)[N:16]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.CN.C[CH2:23][N:24](CC)CC.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCOC(C)=O>[OH:1][C:2]1([C:12]2[S:13][CH:14]=[C:15]([C:17]([NH:24][CH3:23])=[O:19])[N:16]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66786970HCID 66786970, compound

Product 1

HCID 66787107HCID 66787107, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(8-hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)-1,3-thiazole-4-carboxylic acid (0.30 g, 1.05 mmol) and methylamine (2M in THF, 2 mL, 4 mmol) in CH2Cl2 (10 mL) was added Et3N (0.5 mL, 3.6 mmol) followed by EDC (0.242 g, 1.262 mmol) and HOBt (0.193 g, 1.26 mmol). The mixture was stirred at room temperature overnight. Then the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3 and brine. The organic layer was dried (MgSO4), concentrated and flash chromatographed (50% EtOAc/hexanes) to give 0.16 g of the title compound in 50% yield. MS (EI) (M+H)+=299.0.

Workup

  1. washwashed with saturated Na2CO3 and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customflash chromatographed (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-029e40ffe4ac43e5bc65b89231c24723
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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