Ethyl bromoacetate → 3-{(2s,4s)-1-Tert-butoxycarbonyl-4-[n-(4-cyanophenylmethyl)-n-(ethoxycarbonylmethyl)amino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

HRID 1791905Notes

Reaction equation

HRID 1791905 reaction equation
Cl.Cl.[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C@@H:13]2[CH2:17][NH:16][C@H:15]([C:18]([N:20]3[CH2:24][CH2:23][S:22][CH2:21]3)=[O:19])[CH2:14]2)=[CH:7][CH:6]=1)#[N:4].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(N([CH:38]([CH3:40])[CH3:39])CC)(C)C.[C:41](=[O:44])([O-])[OH:42].[Na+].[CH3:46]N1CCCC1=O>>[C:38]([O:42][C:41]([N:16]1[CH2:17][C@@H:13]([N:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=2)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][C@H:15]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:44])([CH3:40])([CH3:46])[CH3:39]

Participants

6

Reactant 5

HCID 7748Ethyl bromoacetateHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 675078123-[(2S,4S)-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine dihydrochloride

Product 1

HCID 675069753-{(2s,4s)-1-Tert-butoxycarbonyl-4-[n-(4-cyanophenylmethyl)-n-(ethoxycarbonylmethyl)amino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

Procedure

The product (0.833 g) of Example 63 (1) was dissolved in N-methyl-2-pyrrolidone (6 mL), and ethyl bromoacetate (0.333 mL) and diisopropylethylamine (1.05 mL) were added thereto. The mixture was stirred at room temperature for 18 hr. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-(ethoxycarbonylmethyl)amino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (1.01 g) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4a2f1cb2330a4ca7b53b094e463eda13
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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