Diisopropylethylamine → HCID 178520737, compound

HRID 1404349Notes

Reaction equation

HRID 1404349 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-aminoethylamino)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-506ed9c813c14fbd9f0498f0094a08ff
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

Loading…