Ethyl bromoacetate → HCID 178525872, compound

HRID 1404348Notes

Reaction equation

HRID 1404348 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][C:9]([NH:11][C@H:12]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([OH:24])=[O:23])[C:15]=3[O:14][B:13]2[OH:25])=[O:10])[CH2:4][CH2:3]1.Br[CH2:27][C:28]([O:30]CC)=[O:29].[OH-].[Na+]>CO>[C:28]([CH2:27][NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][C:9]([NH:11][C@H:12]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([OH:24])=[O:23])[C:15]=3[O:14][B:13]2[OH:25])=[O:10])[CH2:4][CH2:3]1)([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 178511528HCID 178511528, compound

Product 1

HCID 178525872HCID 178525872, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-3-(2-(trans-4-aminocyclohexyl)acetamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid (Example 6) in MeOH was added TEA (2.5 eq), followed by ethyl bromoacetate (1.2 eq). The reaction mixture was stirred at RT overnight. To this reaction mixture was then added 1N NaOH and stirred for 6 hr. After concentration in vacuo, 1N HCl was added to adjust pH to 1. The reaction mixture was purified using reverse phase HPLC to afford the title compound. ESI-MS m/z 405 (MH)+.

Workup

  1. stirringstirred for 6 hr
  2. concentrationAfter concentration in vacuo, 1N HCl
  3. additionwas added
  4. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-219bf9fb704c4e4caca3e902c4431db8
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

Loading…