Triethylamine → 2-[2-(4-Cyclopropyl-phenyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-yl]-propionic acid

HRID 1942221Notes

Reaction equation

HRID 1942221 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:14][CH2:13][C:12]4([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Br[CH:22]([CH3:26])[C:23]([OH:25])=[O:24].CCN(CC)CC>ClCCCl>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:14][CH2:13][C:12]4([CH2:19][CH2:18][N:17]([CH:22]([CH3:26])[C:23]([OH:25])=[O:24])[CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117292-Bromopropionic acidHCID 582872772-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 582872642-[2-(4-Cyclopropyl-phenyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-yl]-propionic acidYield 19.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 200 mg (0.74 mmol) 2-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one, 168 mg (1.11 mmol) 2-bromo-propionic acid and 224 mg (2.21 mmol) NEt3 in 5 mL DCE was heated to 80° C. for 2 h and concentrated. The residue was taken up in methanol and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 49.4 mg (19%) of the title compound. MS m/e: 343.2 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customsubjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and formic acid
  5. additionThe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-79ec2db2d21842a599b263b97595fa8c
Source dataset
uspto-grants-2013_03
Patent number
US08389539B2

Reaction notes

Loading…