Hydrochloric Acid → HCID 67236755, compound

HRID 2364819Notes

Reaction equation

HRID 2364819 reaction equation
[ClH:1].[C:2]([O:5][C@H:6]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([C:15]2[CH:20]=[CH:19][C:18]([NH:21]C(OC(C)(C)C)=O)=[CH:17][CH:16]=2)[N:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@H:7]1[C:36]1[CH:41]=[CH:40][C:39]([NH:42]C(OC(C)(C)C)=O)=[CH:38][CH:37]=1)(=[O:4])[CH3:3].CCOCC>O1CCOCC1>[ClH:1].[ClH:1].[C:12]([O:11][C@H:10]1[C@H:6]([O:5][C:2](=[O:4])[CH3:3])[C@H:7]([C:36]2[CH:37]=[CH:38][C:39]([NH2:42])=[CH:40][CH:41]=2)[N:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@H:9]1[C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 131731307HCID 131731307, compound

Product 1

HCID 67236755HCID 67236755, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4 N hydrogen chloride in dioxane (8 mL) was treated with the compound of Example 70B (136 mg, 0.21 mmol) followed by stirring at RT for 2 h. (During this time, the mono-deprotection product started precipitating, and ca. 4 mL of dichloromethane was added to speed the reaction by solublizing the mono-hydrochloride) The mixture was added to excess ether and the product collected by filtration and washed with ether. After drying in a vacuum oven at 50° C. for 18 h, these procedures afforded the title compound (92 mg, 84%) as an off-white powder. 1H NMR (400 MHz, DMSO-d6) δ 7.28 (m, 8 H), 6.81 (t, J=8.9 Hz, 2 H), 6.33 (m, 2 H), 5.63 (m, 2 H), 5.51 (dd, J=5.5, 1.9 Hz, 2 H), 1.79 (s, 6 H).

Workup

  1. customthe mono-deprotection product started precipitating
  2. additionca. 4 mL of dichloromethane was added
  3. customthe reaction
  4. filtrationthe product collected by filtration
  5. washwashed with ether
  6. customAfter drying in a vacuum oven at 50° C. for 18 h

Sources & evidence

ORD record
ord-840a618d71394983a45be6a23570569e
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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