Benzyl isocyanate → HCID 11374154, compound

HRID 1374550Notes

Reaction equation

HRID 1374550 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:11][C@@H:12]([CH3:33])[C:13]([NH:15][CH:16]1[C:22](=[O:23])[N:21]([CH3:24])[C:20]2[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=2[C:18]2[CH:29]=[CH:30][CH:31]=[CH:32][C:17]1=2)=[O:14]>C1(C)C=CC=CC=1>[CH3:24][N:21]1[C:22](=[O:23])[CH:16]([NH:15][C:13]([C@@H:12]([O:11][C:9](=[O:10])[NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:33])=[O:14])[C:17]2[CH:32]=[CH:31][CH:30]=[CH:29][C:18]=2[C:19]2[CH:28]=[CH:27][CH:26]=[CH:25][C:20]1=2

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 69507835HCID 69507835, compound

Product 1

HCID 11374154HCID 11374154, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Benzylisocyanate (13.3 mg, 0.1 mmol) was added to a solution of (S)-2-hydroxy-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-propionamide (30 mg, 0.1 mmol) in Toluol (1 ml) and heated to 100° C. for 1 week. The solvent was evaporated and the residue was dissolved in DMF (0.5 ml). The title compound, MS: m/e=444.4 (M+H+) (29 mg, 67%), 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-14649a73d2274670bb7e639f16a227cb
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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