Ethyl bromoacetate → HCID 178525872, compound

HRID 1486161Notes

Reaction equation

HRID 1486161 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-0fa4d00e069b46c7b7781b435e42fec9
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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