Hydrochloric Acid → HCID 57116855, compound

HRID 651441Notes

Reaction equation

HRID 651441 reaction equation
Cl.C([N:6]([N:16]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[N+:25]([O-:27])=[O:26])[C:17]1=[O:28])[C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[NH2:11])(C)(C)C.CCOCC>C(Cl)Cl>[O:28]=[C:17]1[C:18]2[C:23](=[C:22]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:20][CH:19]=2)[CH2:24][N:16]1[NH:6][C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[NH2:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67018347HCID 67018347, compound

Product 1

HCID 57116855HCID 57116855, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas was bubbled into a stirred 5° C. solution of t-butyl N-(1-oxo-4-nitro-isoindolin-2-yl)-L-glutamine (3.6 g, 9.9 mmol) in methylene chloride (60 mL) for 1 hour. The mixture was then stirred at room temperature for another hour. Ether (40 mL) was added and the resulting mixture was stirred for 30 minutes. The slurry was filtered, washed with ether and dried to afford 3.3 g of the product: 1H NMR (DMSO-d6) δ8.45(d, J=8.1 Hz, 1H), 8.15(d, J=7.5 Hz, 1H), 7.83(t, J=7.9 Hz, 1H), 7.24(s, 1H), 6.76(s, 1H), 4.93(s, 2H), 4.84-4.78(dd, J=4.8 amd 10.4 Hz, 1H), 2.34-2.10(m, 4H); 13C NMR (DMSO-d6) δ173.03, 171.88, 165.96, 143.35, 137.49, 134.77, 130.10, 129.61, 126.95, 53.65, 48.13, 31.50, 24.69; Anal. Calcd for C13H13N3O6: C, 50.82; H, 4.26; N, 13.68. Found: C, 50.53; H, 4.37; N, 13.22.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. filtrationThe slurry was filtered
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-a0432b61243143e987760718ab9712ce
Source dataset
uspto-grants-2001_08
Patent number
US06281230B1

Reaction notes

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