1,2-Dichloroethane → HCID 67417455, compound

HRID 1803511Notes

Reaction equation

HRID 1803511 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:19]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13](=[O:15])[NH:26][CH2:25][CH2:24][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:11]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27559293-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Product 1

HCID 67417455HCID 67417455, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(tert-Butoxycarbonylamino-methyl)-benzoic acid (500 mg, 1.99 mmol), 2-Pyrrolidin-1-yl-ethylamine (0.28 mL, 2.19 mmol), EDC (459 mg, 2.39 mmol), HOBt (323 mg, 2.39 mmol) and triethylamine (0.40 mL, 2.99 mmol) in DMF (10 mL) was stirred at ambient temperature for 15 h. The mixture was diluted with EtOAc (25 mL) and washed with water (25 mL) and NaHCO3 (25 mL). The aqueous mixture was extracted with EtOAc (2×25 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to yield the title compound (403 mg, 58%). m/z (M+1) 348.21.

Workup

  1. washwashed with water (25 mL) and NaHCO3 (25 mL)
  2. extractionThe aqueous mixture was extracted with EtOAc (2×25 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7cf8fa5b478a4ce6b8455f98dcd8d481
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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