Acetic Acid → HCID 178457401, compound

HRID 1486205Notes

Reaction equation

HRID 1486205 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([NH:14][C@H:15]2[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:18]=3[O:17][B:16]2[OH:28])=[O:13])[CH2:7][CH2:6]1.C(O)(=O)C.[CH3:33][C:34]([CH3:36])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[OH:28][B:16]1[C@@H:15]([NH:14][C:12](=[O:13])[CH2:11][C@H:8]2[CH2:9][CH2:10][C@H:5]([NH:4][CH2:3][CH2:2][NH:1][CH:34]([CH3:36])[CH3:33])[CH2:6][CH2:7]2)[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:18]=2[O:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 178511351HCID 178511351, compound

Product 1

HCID 178457401HCID 178457401, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-3-(2-(trans-4-(2-aminoethylamino)cyclohexyl)acetamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid from Example 15 (92 mg) in MeOH (2 mL) was added TEA (70 μL), acetic acid (30 μL), acetone (0.1 mL) and sodium triacetoxyborohydride (212 mg). The reaction mixture was stirred overnight at RT. Solvent was removed and the product was purified using reverse phase HPLC to afford the titled compound. ESI-MS m/z 432 (MH)+.

Workup

  1. customSolvent was removed
  2. customthe product was purified

Sources & evidence

ORD record
ord-82b953daaa8f4ea4bc6c299bf675ccfb
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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