1,2-Dichloroethane → HCID 178453836, compound

HRID 2089049Notes

Reaction equation

HRID 2089049 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1.[C:17]([O:21][C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:10][CH2:11][C@H:12]([NH:15][C:26](=[O:27])[CH2:25][NH:24][C:22](=[O:23])[O:21][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:13][CH2:14]2)[CH:5]=[C:4]([I:16])[CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 178511613HCID 178511613, compound

Product 1

HCID 178453836HCID 178453836, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 213a (3.950 g, 11.23 mmol), 2-(tert-butoxycarbonylamino)acetic acid (2.165 g, 12.36 mmol), HOBT (1.892 g, 12.36 mmol), EDC (2.369 g, 12.36 mmol), and triethylamine (2.04 mL, 14.6 mmol) in tetrahydrofuran (100 mL) was stirred at room temperature for 3 hours. The reaction was diluted with 50% brine and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was triturated with EtOAc/hexane (8:2) to give 2.756 g of the title compound. The filtrate was purified on an 80 g column using the ISCO Companion flash system eluting with EtOAc/hexane (7:3 to 8:2) to give the 1.091 g more title compound.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with EtOAc/hexane (8:2)

Sources & evidence

ORD record
ord-ee8aab3f9c8246ac89aa0d318849a2a1
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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