Diisopropylethylamine → HCID 178520737, compound

HRID 1486162Notes

Reaction equation

HRID 1486162 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.[CH3:29]CN(C(C)C)C(C)C.Cl.C(=N)OC(C)C>CO>[N:4]1([C@H:5]2[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([NH:14][C@H:15]3[CH2:20][C:19]4[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:18]=4[O:17][B:16]3[OH:28])=[O:13])[CH2:7][CH2:6]2)[CH2:3][CH2:2][N:1]=[CH:29]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12801779Propan-2-yl methanimidate--hydrogen chloride (1/1)HCID 178511351HCID 178511351, compound

Product 1

HCID 178520737HCID 178520737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-3-(2-(trans-4-(2-amino ethylamino)cyclohexyl)acetamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid (Example 15) in MeOH was added DIEA (2.5 eq), followed by isopropyl formimidate hydrochloride (1.2 eq). The reaction mixture was stirred at RT overnight. The mixture was then concentrated in vacuo and the crude product was purified using reverse phase HPLC to afford the title compound. ESI-MS m/z 400 (MH)+.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-fe352b97928b42d48e9e066a174bc8fb
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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