1,2-Dichloroethane → HCID 178523384, compound

HRID 479282Notes

Reaction equation

HRID 479282 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][NH:10][S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:5][CH2:4]1.C(Cl)CCl.[CH2:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH:29]1[C:38](O)=[O:39]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[S:11]([NH:10][CH2:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([CH2:2][NH:1][C:38]([CH:29]2[CH2:30][CH2:31][C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:28]2)=[O:39])[CH2:4][CH2:5]1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 178511246HCID 178511246, compound

Product 1

HCID 178523384HCID 178523384, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of naphthalene-2-sulfonic acid-(4-aminomethyl-trans-cyclohexylmethyl)amide (0.5 g, 1.4 mmol), EDC (0.54 g, 2.8 mmol), and DMAP (0.34 g, 2.8 mmol) in methylene chloride (30 mL) was stirred at room temperature for 0.5 h. 1,2,3,4-tetrahydronaphthalen-2-carboxylic acid (0.24 g, 1.4 mmol) was added to the reaction mixture and stirred at room temperature till the completion of the reaction (by TLC). The reaction mixture was washed with saturated ammonium chloride (3×30 mL), dried over sodium sulfate and concentrated in vacuo. The residue was flash chromatographed over silica gel to afford white solid (0.66 g, 99%); mp 225-6° C.

Workup

  1. stirringstirred at room temperature till the completion of the reaction (by TLC)
  2. washThe reaction mixture was washed with saturated ammonium chloride (3×30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customchromatographed over silica gel

Sources & evidence

ORD record
ord-7b1a89cfc29647c88c04197e11afa169
Source dataset
uspto-grants-2003_11
Patent number
US06645774B1

Reaction notes

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