tert-butyl N-(2-oxoethyl)carbamate → HCID 178453691, compound

HRID 1486152Notes

Reaction equation

HRID 1486152 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.O=[CH:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>CO.[Pd]>[C:32]([O:31][C:30]([NH:29][CH2:28][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)=[O:36])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 178511528HCID 178511528, compound

Product 1

HCID 178453691HCID 178453691, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 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, 15 mg) in MeOH (2 mL) was added tert-butyl 2-oxoethylcarbamate (20 mg). Pd/C (10% by weight, 10 mg) was added and the reaction mixture was stirred under H2 balloon overnight. The reaction mixture was filtrated and the solvent was then removed under reduced pressure and the residue was carried on to the next step without further purification. ESI-MS m/z 490.1 (MH)+.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customthe solvent was then removed under reduced pressure
  3. customthe residue was carried on to the next step without further purification

Sources & evidence

ORD record
ord-29675c174f2340f8a413ae76d71607c2
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

Loading…