Hydrochloric Acid → 2-(1-Methylsulfanyl-2-phenethylcarbamoyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1582732Notes

Reaction equation

HRID 1582732 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([S:19][CH3:20])[CH:14]([C:16]([OH:18])=O)[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.C1C=C2N=NN(O)C2=CC=1.O.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([S:19][CH3:20])[CH:14]([C:16](=[O:18])[NH:29][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 693253742-(2-Carboxy-1-methylsulfanyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 695513572-(1-Methylsulfanyl-2-phenethylcarbamoyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the crude 2-(2-carboxy-1-methylsulfanyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (223 mg) obtained above in CH2Cl2 (3 ml) was added phenethylamine(0.18 ml, 1.41 mmol), WSCI monohydrochloride(203 mg, 1.06 mmol), HOBt monohydrate(162 mg, 1.06 mmol) and diisopropylethylamine(0.37 ml, 2.12 mmol) at room temperature. After being stirred at room temperature for 4.5 hr, the mixture was quenched with 1N HCl (20 ml), extracted with AcOEt, dried (MgSO4) and concentrated in vacuo to give a crude oil, which was purified by flash column chromatography (hexane:AcOEt=3:1) to give 2-(1-methylsulfanyl-2-phenethylcarbamoyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as an oil(123 mg, 43%).

Workup

  1. customthe mixture was quenched with 1N HCl (20 ml)
  2. extractionextracted with AcOEt
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a crude oil, which
  6. customwas purified by flash column chromatography (hexane:AcOEt=3:1)

Sources & evidence

ORD record
ord-20f8d75f2edb4f4d8d44c349e813191a
Source dataset
uspto-grants-2004_05
Patent number
US06737409B2

Reaction notes

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