1-Hydroxybenzotriazole → HCID 90037260, compound

HRID 1055381Notes

Reaction equation

HRID 1055381 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][S:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:22])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][S:14][C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][C:16]=2[NH:22][C:10]1=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90036907HCID 90036907, compound

Product 1

HCID 90037260HCID 90037260, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-2-tert-butoxycarbonylamino-3-(2,6-diamino-phenylsulfanyl)-propionic acid (1.0 g, 3.1 mmol) in DMF (12 mL) was added DIEA (1.6 mL, 9.1 mmol), HOBT.H2O (859 mg, 6.2 mmol) and HBTU (2.3 g, 6.2 mmol). The mixture was stirred under an atmosphere of N2 at room temperature for 3 h. The reaction was poured into H2O and extracted with EtOAc. The organic extracts were combined, washed with 0.5 M HCl, H2O, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography by silica gel chromatography to give the title compound (560 mg, 59%).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with 0.5 M HCl, H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography by silica gel chromatography

Sources & evidence

ORD record
ord-d84bdd5654ae43dfbcd0912633e4a4c4
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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