Triethylamine → (3R*,4R*)-3-{[Cyclopropyl-(pyrrolidine-1-carbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158433Notes

Reaction equation

HRID 1158433 reaction equation
C(N(CC)CC)C.[N:8]1([C:13](Cl)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1.[C:16]([O:20][C:21]([N:23]1[CH2:27][C@@H:26]([CH2:28][N:29]([CH:46]([CH3:48])[CH3:47])[C:30](=[O:45])[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[C@H:25]([CH2:49][NH:50][CH:51]2[CH2:53][CH2:52]2)[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[C:16]([O:20][C:21]([N:23]1[CH2:27][C@@H:26]([CH2:28][N:29]([CH:46]([CH3:47])[CH3:48])[C:30](=[O:45])[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[C@H:25]([CH2:49][N:50]([CH:51]2[CH2:52][CH2:53]2)[C:13]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:14])[CH2:24]1)=[O:22])([CH3:18])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709371-Pyrrolidinecarbonyl chlorideHCID 68616408(3R*,4R*)-3-Cyclopropylaminomethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68617025(3R*,4R*)-3-{[Cyclopropyl-(pyrrolidine-1-carbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Triethylamine (99 μL, 0.714 mmol) followed by 1-pyrrolidinecarbonyl chloride is added to a solution of ((3R*,4R*)-3-cyclopropylaminomethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (254 mg, 0.476 mmol) in CH2Cl2 (20 mL). The resulting solution is stirred at RT for 2 h and at 60° C. for another 24 h. Evaporation of the solvent affords the crude product which is purified by preparative HPLC (Waters C18 ODB, eluent: H2O/CH3CN 20 to 100%) to give the title compound. MS (LC-MS): 631.1 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 6.31 min.

Workup

  1. customEvaporation of the solvent
  2. customaffords the crude product which
  3. customis purified by preparative HPLC (Waters C18 ODB, eluent: H2O/CH3CN 20 to 100%)

Sources & evidence

ORD record
ord-a9245f7806b34ee8879a84398480a6da
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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