1,2-Dichloroethane → HCID 178502728, compound

HRID 579563Notes

Reaction equation

HRID 579563 reaction equation
C(Cl)CCl.[CH2:5]([O:12][C:13]([NH:15][C@@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=O)[CH2:18][CH2:17]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH3:26][NH:27][O:28][CH3:29].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.C1C=CC2N(O)N=NC=2C=1.O>[CH3:29][O:28][N:27]([CH3:26])[C:22]([C@@H:19]1[CH2:18][CH2:17][C@H:16]([NH:15][C:13](=[O:14])[O:12][CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:21][CH2:20]1)=[O:24]

Participants

9

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 178523780HCID 178523780, compound

Product 1

HCID 178502728HCID 178502728, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 757711-HydroxybenzotriazoleCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

EDC (6.9 g, 36 mmol) was added in several portions to a stirring solution of cis-4-benzyloxycarbonylamino-cyclohexanecarboxylic acid (5.0 g, 18 mmol), DMAP (10 mg), HOBt (10 mg) and N,O-dimethylhydroxylamine hydrochloride (3.5 g, 36 mmol) in dichloromethane (100 mL). To this solution was added dropwise triethylamine (10 mL, 72.0 mmol), and the reaction mixture was allowed to stir at room temperature overnight. After completion of stirring, the reaction mixture was poured into water and the aqueous layer was extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give benzyl cis-4-(methoxy(methyl)carbamoyl)cyclohexylcarbamate as a colorless oil (5.48 g, 17.1 mmol, 95%). 1H NMR (CDCl3, 300 MHz) δ 7.38-7.28 (m, 5H), 5.09 (bs, 2H), 5.02 (m, 1H), 3.92-3.82 (m, 1H), 3.69 (s, 3H), 3.17 (s, 3H), 2.81-2.68 (m, 1H), 1.91-1.78 (m, 2H), 1.74-1.6 (m, 6H).

Workup

  1. stirringAfter completion of stirring
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5aae5745d6fc49478deaa7f3912c58a9
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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