Hydrochloric Acid → HCID 57116855, compound

HRID 1823827Notes

Reaction equation

HRID 1823827 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) δ 8.45(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 and 10.4 Hz, 1H), 2.34–2.10(m, 4H); 13C NMR (DMSO-d6) δ 173.03, 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-5f8396355c164dd6b2667752ae72e59c
Source dataset
uspto-grants-2006_05
Patent number
US07041680B2

Reaction notes

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