(S)-(9H-fluoren-9-yl)methyl 1-(2-(4-methoxybenzyl)-8-chloro-1-oxo-1,2-dihydroisoquinolin-3-yl)ethylcarbamate → HCID 68746456, compound

HRID 518263Notes

Reaction equation

HRID 518263 reaction equation
COC1C=CC(C[N:8]2[C:17]([C@@H:18]([NH:20][C:21](=[O:37])[O:22][CH2:23][CH:24]3[C:36]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:30]4[C:25]3=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH3:19])=[CH:16][C:15]3[C:10](=[C:11]([Cl:38])[CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:39])=CC=1>FC(F)(F)C(O)=O>[Cl:38][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[C:9](=[O:39])[NH:8][C:17]([C@@H:18]([NH:20][C:21](=[O:37])[O:22][CH2:23][CH:24]1[C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:30]3[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH3:19])=[CH:16]2

Participants

3

Reactant 1

HCID 71232890(S)-(9H-fluoren-9-yl)methyl 1-(2-(4-methoxybenzyl)-8-chloro-1-oxo-1,2-dihydroisoquinolin-3-yl)ethylcarbamate

Product 1

HCID 68746456HCID 68746456, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-2-(4-methoxybenzyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)ethylcarbamate (344) (80 g, 142 mmol, 1.0 eq) was dissolved in 2,2,2-trifluoroacetic acid (300 mL) and the resulting mixture was stirred at reflux for 2 h. The mixture was allowed to cool to RT and then concentrated in vacuo. The residue was poured into water and then neutralized with NH3.H2O to adjust the pH value to 6-7 under 0° C. The resulting mixture was stirred at RT for 30 min. The solid was collected by filtration, rinsed with water (2×50 mL) and dried in vacuo to afford (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-oxo-1,2-dihydroisoquinolin-3-yl)ethylcarbamate (345).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was poured into water
  4. customunder 0° C
  5. stirringThe resulting mixture was stirred at RT for 30 min
  6. filtrationThe solid was collected by filtration
  7. washrinsed with water (2×50 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c309cda9541c465c8660319e45d8c34b
Source dataset
uspto-grants-2015_08
Patent number
US09115141B2

Reaction notes

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