1,2-Dichloroethane → HCID 58333591, compound

HRID 2066849Notes

Reaction equation

HRID 2066849 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]([C:28](O)=[O:29])=[CH:23][C:22]=3[F:31])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C[O:33][C:34](=[O:37])[CH2:35][NH2:36].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>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]([C:28](=[O:29])[NH:36][CH2:35][C:34]([OH:33])=[O:37])=[CH:23][C:22]=3[F:31])[CH2:19][CH2:20]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 69221Glycine methyl esterHCID 757711-HydroxybenzotriazoleHCID 58333593HCID 58333593, compound

Product 1

HCID 58333591HCID 58333591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-1 (32 mg, 0.073 mmol), amino-acetic acid methyl ester (0.11 mmol) and HOBT (15 mg, 0.11 mmol) were combined in DCM (1 mL) and stirred at room temperature for 10 minutes. EDC(19 mg, 0.1 mmol) was added and the mixture was stirred for 18 h. The solution was washed with 2 mL of aqueous NaHCO3, concentrated and taken up with 0.5 mL of dioxane. 0.5 mL of 1N NaOH was added and the mixture was stirred at 60° C. for 1 h. It was then cooled to room temperature, acidified with 0.5 mL of 2N HCl and extracted with ethyl acetate (1.5 mL). The organic layer was concentrated under a stream of nitrogen and purified on preparative HPLC to give 30-1: LC-MS 497.4 (MH).

Workup

  1. stirringthe mixture was stirred for 18 h
  2. washThe solution was washed with 2 mL of aqueous NaHCO3
  3. concentrationconcentrated
  4. addition0.5 mL of 1N NaOH was added
  5. stirringthe mixture was stirred at 60° C. for 1 h
  6. temperatureIt was then cooled to room temperature
  7. extractionextracted with ethyl acetate (1.5 mL)
  8. concentrationThe organic layer was concentrated under a stream of nitrogen
  9. custompurified on preparative HPLC
  10. customto give 30-1

Sources & evidence

ORD record
ord-f9ce94e424654746bb5bbb383a37d5e8
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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