Hydrochloric Acid → HCID 21309716, compound

HRID 617314Notes

Reaction equation

HRID 617314 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.[ClH:21]>>[ClH:21].[ClH:21].[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][NH:11]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21309664HCID 21309664, compound

Product 1

HCID 21309716HCID 21309716, compoundYield 63%

Procedure

The compound from step 40a (0.123 g, 0.44 mmol) was treated with saturated ethanolic HCl (5 mL) for 18 hr. The volatiles were removed in vacuo, and the dihydiochloride was washed with Et2O (3×20 mL), evaporated to dryness and recrystallized (EtOHIEt2O) to yield the title compound (0.074 g, 63%) as a white solid. mp 141-144° C. MS (DCI/NH3) m/e: 179 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.33 (d, J=2.9 Hz, 1H), 7.89 (dd, J=9.0, 2.8 Hz, 1H), 7.64 (d J=8.8 Hz, 1H), 5.01-4.93 (m, 1H), 4.48 (d, J=4.4 Hz, 2H), 4.21-4.04 (m, 2H), 2.70 (q, J=8.5 Hz, 2H), 2.62 (s, 3H). Anal. calc. for C10H16Cl2N2O.1.0H2O: C, 44.62; H, 6.74; N, 10.41. Found: C, 44.55; H, 7.02; N, 10.50. [α]D24 -7.89 ° (c=0.19 in MeOH).

Workup

  1. customThe volatiles were removed in vacuo
  2. washthe dihydiochloride was washed with Et2O (3×20 mL)
  3. customevaporated to dryness
  4. customrecrystallized (EtOHIEt2O)

Sources & evidence

ORD record
ord-7a0afdf95eb1444dafaf5ff673653586
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

Loading…