Hydrochloric Acid → N-[(3R*,4R*)-1-Benzyl-4-(isopropylamino-methyl)-pyrrolidin-3-ylmethyl]-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide

HRID 1158485Notes

Reaction equation

HRID 1158485 reaction equation
C(OC(=O)[N:7]([CH2:11][C@H:12]1[C@@H:16]([CH2:17][N:18]([CH:35]([CH3:37])[CH3:36])[C:19](=[O:34])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:21]=2)[CH2:15][N:14]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:13]1)[CH:8]([CH3:10])[CH3:9])(C)(C)C.Cl>O1CCOCC1>[CH2:38]([N:14]1[CH2:13][C@@H:12]([CH2:11][NH:7][CH:8]([CH3:10])[CH3:9])[C@@H:16]([CH2:17][N:18]([CH:35]([CH3:37])[CH3:36])[C:19](=[O:34])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:21]=2)[CH2:15]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59512411[(3S*,4R*)-1-Benzyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidin-3-ylmethyl]-isopropyl-carbamic acid tert-butyl ester

Product 1

HCID 59512319N-[(3R*,4R*)-1-Benzyl-4-(isopropylamino-methyl)-pyrrolidin-3-ylmethyl]-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of [(3S*,4R*)-1-benzyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidin-3-ylmethyl]-isopropyl-carbamic acid tert-butyl ester (0.41 g, 0.66 mmol), is added a dioxane solution of HCl 4N (10 mL). The reaction mixture is stirred for 2 h at room temperature. The solvent is concentrated and water (20 mL), an aqueous solution of NaOH 4N (5 mL) and Et2O (25 mL) are added. The layers are separated and the aqueous one extracted twice with Et2O. The combined organic extracts are dried (MgSO4), and the solvent is removed in vacuo to give the title compound which is used without further purification in the next step. MS (LC-MS): 526.4 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.53 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.78 min.

Workup

  1. concentrationThe solvent is concentrated
  2. additionwater (20 mL), an aqueous solution of NaOH 4N (5 mL) and Et2O (25 mL) are added
  3. customThe layers are separated
  4. extractionthe aqueous one extracted twice with Et2O
  5. dry with materialThe combined organic extracts are dried (MgSO4)
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-fb7d4b704157403aa6335ec8f7a56afc
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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