1,2-Dichloroethane → HCID 86616984, compound

HRID 1944564Notes

Reaction equation

HRID 1944564 reaction equation
C([N:4]([CH:7]([CH3:9])C)[CH2:5][CH3:6])(C)C.[CH3:10][O:11][CH2:12][C:13]([OH:15])=O.[CH:16]1[CH:21]=N[C:19]2N(O)N=N[C:18]=2[CH:17]=1.[CH2:26](Cl)[CH2:27]Cl.[CH:30](Cl)(Cl)Cl>>[CH2:7]([N:4]([CH2:5][C@@H:6]1[CH2:30][C@H:26]1[CH3:27])[C:13](=[O:15])[CH2:12][O:11][CH3:10])[C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:21]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6212ChloroformHCID 12251Methoxyacetic AcidHCID 81531DiisopropylethylamineHCID 181649HOAt

Product 1

HCID 86616984HCID 86616984, compound

Procedure

To a solution of N-benzyl-1-(2-trans-methylcyclopropyl)methanamine hydrochloride (intermediate 3.2.1, 10 g, 47.2 mmol) in CHCl3 (150 mL) was added diisopropylethyl amine (9.87 mL, 56.7 mmol), methoxyacetic acid (4.35 mL, 56.7 mmol), HOAt (1.29 g, 9.5 mmol) and EDC (10.87 g, 56.7 mmol), and the reaction mixture was stirred at rt for 18 h. The reaction mixture was concentrated in vacuo, diluted with EtOAc, washed with 10% KHSO4, aq NaHCO3 and brine, dried over sodium sulfate and concentrated in vacuo to give trans N-benzyl-2-methoxy-N-[(2-methylcyclopropyl)methyl]acetamide which was used as is in the next step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with 10% KHSO4, aq NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fd8d4d2a3844abd9a1c237258d70969
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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