Triethylamine → HCID 11394910, compound

HRID 1374551Notes

Reaction equation

HRID 1374551 reaction equation
[OH:1][C@@H:2]([CH3:23])[C:3]([NH:5][CH:6]1[C:12](=[O:13])[N:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2)=[O:4].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:26].[CH2:37]([N:39]([CH2:42]C)CC)[CH3:38].Cl.C(N)C>C1(C)C=CC=CC=1>[CH3:14][N:11]1[C:12](=[O:13])[CH:6]([NH:5][C:3]([C@@H:2]([O:1][C:42](=[O:26])[NH:39][CH2:37][CH3:38])[CH3:23])=[O:4])[C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]1=2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 821294-Nitrophenyl chloroformateHCID 69507835HCID 69507835, compound

Product 1

HCID 11394910HCID 11394910, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (S)-2-hydroxy-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-propionamide (30 mg, 0.09 mmol), 4-nitrophenyl chloroformate (19 mg, 0.09 mmol), and triethylamine (20 microliter) in toluol (1 ml) were shaken overnight at r.t. Ethylamine hydrochloride (7.9 mg, 0.1 mmol) was added and the mixture was shaken again overnight at r.t. The solvent was evaporated and the residue was dissolved in DMF (0.5 ml). The title compound, MS: m/e=382.3 (M+H+), (11 mg, 30%) was isolated from this mixture by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5–95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 30 ml/min).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in DMF (0.5 ml)

Sources & evidence

ORD record
ord-d434922c9ce949ebbf87ec87e3b6a64e
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

Loading…