Water → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-cyclopentane carboxylic acid diisopropylethylamine salt

HRID 1445407Notes

Reaction equation

HRID 1445407 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:19][CH:18]3[CH2:20][CH:15]2[C:16](=[O:21])[O:17]3)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[CH3:22][CH2:23][N:24]([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26].[OH2:31]>>[CH:25]([N:24]([CH:28]([CH3:30])[CH3:29])[CH2:23][CH3:22])([CH3:27])[CH3:26].[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:19][CH:18]([OH:17])[CH2:20][CH:15]2[C:16]([OH:21])=[O:31])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 962WaterHCID 81531DiisopropylethylamineHCID 668704341-[(3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carbonyl)-amino]-2-vinyl-cyclo-propane carboxylic acid ethyl ester

Product 1

HCID 668702712-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-cyclopentane carboxylic acid diisopropylethylamine salt

Conditions

Temperature
40 °C

Procedure

To a solution of 3 (800 mg, 2.73 mmol) in water (15 ml) in a 20 ml microwave reaction vessel was added DIPEA (1.2 ml, 6.8 mmol) and a stir bar. The reaction vessel was sealed and the immiscible slurry was shaken vigorously before insertion in the microwave cavity. After 1 min of pre-stirring, the reaction was irradiated for 40 min to a set temperature of 100° C. After cooling to 40° C., the transparent solution was concentrated in vacuo, and the residual brown oil co-evaporated 3 times with acetonitrile to remove any residual water. The crude product 4, in the form of a DIPEA salt, was immediately taken forward to the next step. LC/MS (Method A): tR=1.29 min, >95%, m/z (ESI+)=312 (MH+).

Workup

  1. customThe reaction vessel was sealed
  2. stirringAfter 1 min of pre-stirring
  3. customthe reaction was irradiated for 40 min to a set temperature of 100° C
  4. concentrationthe transparent solution was concentrated in vacuo
  5. customto remove any residual water

Sources & evidence

ORD record
ord-b34bc49236284e6db72c831e99f5136d
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

Loading…