Nitrogen → HCID 59819863, compound

HRID 383605Notes

Reaction equation

HRID 383605 reaction equation
N#N.CCN(CC)CC.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:22][CH2:23][C:24]([OH:26])=O)[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].[CH3:27][O:28][C:29]([C@H:31]1[CH2:36][CH2:35][C@@H:34]([NH2:37])[CH2:33][CH2:32]1)=[O:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:27][O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([NH:37][C:24](=[O:26])[CH2:23][CH2:22][C:14]2[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:12]([O:11][CH3:10])[CH:13]=2)[CH2:33][CH2:32]1)=[O:30]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 648603,4,5-Trimethoxyhydrocinnamic acidHCID 178501206HCID 178501206, compound

Product 1

HCID 59819863HCID 59819863, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(The following reaction is done in an anhydrous N2 atmosphere.) Suspend EDCHCl (175 mg, 0.91 mmol) and Et3N (127 μL, 0.91 mmol) in anhydrous DCM (8.0 mL) and stir the resulting solution for 5 min at rt. Add 3-(3,4,5-Trimethoxy-phenyl)-propionic acid (219 mg, 0.91 mmol) and DMAP (22 mg, 0.18 mmol) and stir the resulting solution for 10 min. Add cis-4-Amino-cyclohexanecarboxylic acid methyl ester (74) (136 mg, 0.87 mmol) and stir the reaction solution 2d at rt Remove solvent and purify the crude product by flash chromatography (silica gel, EtOAc/CyH 3+1, later EtOAc) to obtain cis-{4-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-cyclohexanecarboxylic acid methyl ester (75) (254 mg, 76%) as a colorless viscous oil. 1H NMR (400 MHz, CDCl3): 1.40-1.51 (m, 2 H); 1.59-1.70 (m, 4H); 1.70-1.82 (m, 2H); 2.40-2.48 (m, 3H); 2.88 (t, 2H, J=7.6 Hz); 3.65 (s, 3H); 3.79 (s, 3H); 3.82 (s, 6H); 3.86-3.95 (m, 1H); 5.33 (br.d, 1H, J=7.3 Hz); 6.40 (s, 2H).

Workup

  1. custom(The following reaction
  2. customRemove solvent
  3. custompurify the crude product by flash chromatography (silica gel, EtOAc/CyH 3+1, later EtOAc)

Sources & evidence

ORD record
ord-b90b5f2ce7dd499bbfa6c107739353ee
Source dataset
uspto-grants-2013_02
Patent number
US08367677B2

Reaction notes

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