Diisopropylethylamine → HCID 178512226, compound

HRID 1486163Notes

Reaction equation

HRID 1486163 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.C[CH2:27][N:28](C(C)C)C(C)C.Cl.C(=N)OC(C)C>CO>[CH:27](=[NH:28])[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

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12801779Propan-2-yl methanimidate--hydrogen chloride (1/1)HCID 178511528HCID 178511528, compound

Product 1

HCID 178512226HCID 178512226, compound

Reagents, catalysts & solvents 1

HCID 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) 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 374 (MH)+.

Workup

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

Sources & evidence

ORD record
ord-4422b9bc2a484ea8aeff854467816020
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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