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

HRID 1404339Notes

Reaction equation

HRID 1404339 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-9fb8dee2918f4ce99028b83dc8a73186
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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