Hydrochloric Acid → HCID 69003862, compound

HRID 749934Notes

Reaction equation

HRID 749934 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:33]>O1CCOCC1>[ClH:33].[F:31][C:29]([F:30])([F:32])[O:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:16][CH:17]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68997831HCID 68997831, compound

Product 1

HCID 69003862HCID 69003862, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the product from step 3 (0.23 g, 0.51 mmol) was added 4 M HCl in dioxane (5 mL). The resulting mixture was stirred at ambient temperature overnight. The solvent was removed in vacuo. The crude product was triturated with ether and dried under reduced pressure to afford the title product (0.12 g, 61%) as a light green oil; 1H NMR (400 MHz, DMSO-d6) δ 1.74 (m, 1H), 1.94 (m, 2H), 2.12 (m, 1H), 3.22 (m, 2H), 3.89 (m, 1H), 4.15 (m, 1H), 4.25 (dd, J1=3.8 Hz, J2=10.8 Hz, 1H), 7.00-7.10 (m, 6H), 7.36 (d, J=8.4 Hz, 2H), 9.32 (br s, 1H); MS (m/z) 354.5 (M+1); LC (98.4%); HPLC (99.7%).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude product was triturated with ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-9717b3601779426b8362a7646709a789
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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