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

HRID 1829113Notes

Reaction equation

HRID 1829113 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-931dbdfcb8d74771a63f130fca68d895
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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