1-Hydroxybenzotriazole → HCID 67386290, compound

HRID 1898572Notes

Reaction equation

HRID 1898572 reaction equation
[C:1]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[NH:15]1[CH2:18][CH:17]([C:19]#[N:20])[CH2:16]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([CH3:10])[C:11]([N:15]1[CH2:18][CH:17]([C:19]#[N:20])[CH2:16]1)=[O:13])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45072465Azetidine-3-carbonitrile hydrochloride

Product 1

HCID 67386290HCID 67386290, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask were combined Boc-D-alanine (500 mg, 2.64 mmol), azetidine-3-carbonitrile hydrochloride (376 mg, 3.17 mmol), HOBT (445 mg, 2.91 mmol) and HATU (1.11 g, 2.91 mmol). Then added DMF (5 mL) followed by N,N-diisopropylethylamine (1.38 mL, 7.93 mmol). The yellow reaction mixture was stirred at room temperature for 3 h then quenched with water and extracted with EtOAc (3×). The combined organics were washed with water (3×) dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes) to afford 493 mg (74%) of [(R)-2-(3-cyanoazetidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester as a white solid.

Workup

  1. customIn a round-bottomed flask were combined
  2. customthen quenched with water
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with water (3×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-60a55613f5aa428db122db3e19d158b0
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…