Triethylamine → HCID 59512411, compound

HRID 1158484Notes

Reaction equation

HRID 1158484 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:11][C@H:12]1[C@@H:16]([CH2:17][NH:18][CH:19]([CH3:21])[CH3:20])[CH2:15][N:14]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:13]1)[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:30][O:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][C:33]=1[O:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46].C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOCC.O>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:11][C@H:12]1[C@@H:16]([CH2:17][N:18]([CH:19]([CH3:21])[CH3:20])[C:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([O:31][CH3:30])=[C:33]([O:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46])[CH:34]=2)[CH2:15][N:14]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:13]1)[CH:8]([CH3:10])[CH3:9])([CH3:2])([CH3:4])[CH3:3]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 190395024-Methoxy-3-(3-methoxypropoxy)benzoic acidHCID 221413011-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride hydrochlorideHCID 68618327HCID 68618327, compound

Product 1

HCID 59512411HCID 59512411, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of [(3S*,4S*)-1-benzyl-4-(isopropylamino-methyl)-pyrrolidin-3-ylmethyl]-isopropyl-carbamic acid tert-butyl ester (0.32 g, 0.55 mmol), 4-methoxy-3-(3-methoxy-propoxy)-benzoic acid (0.23 g, 0.96 mmol), DMAP (0.12 g, 0.96 mmol), and triethyl-amine (0.56 mL, 0.96 mmol) in DMF (10 mL), is added EDCl-HCl (0.19 g, 0.96 mmol) at 0° C. The reaction mixture is stirred overnight at room temperature. Water and Et2O are added, the layers are separated and the aqueous one is extracted twice with Et2O. The combined organic extracts are dried (MgSO4), and the solvent is removed in vacuo. The crude product is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 90:10) to give the title product. TLC, Rf (CH2Cl2/MeOH 9:1)=0.72. MS (LC-MS): 626.4 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 6.28 min.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous one is extracted twice with Et2O
  3. dry with materialThe combined organic extracts are dried (MgSO4)
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 90:10)

Sources & evidence

ORD record
ord-f7184b90a2e54640ab375ecae0675027
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…