Hydrochloric Acid → HCID 136350767, compound

HRID 2375102Notes

Reaction equation

HRID 2375102 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([N:33](C)[C:34](=O)OC(C)(C)C)[C:10](=[O:32])[NH:11][C:12]2[CH:13]=[C:14]3[C:30](=[O:31])[NH:29][N:28]=[CH:27][C:16]4=[C:17]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[NH:18][C:19]([CH:20]=2)=[C:15]34)=[CH:4][CH:3]=1.[ClH:42].C(N(CC)CC)C>O1CCOCC1>[ClH:42].[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33][CH3:34])[C:10]([NH:11][C:12]2[CH:13]=[C:14]3[C:30](=[O:31])[NH:29][N:28]=[CH:27][C:16]4=[C:17]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[NH:18][C:19]([CH:20]=2)=[C:15]34)=[O:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 136181628HCID 136181628, compound

Product 1

HCID 136350767HCID 136350767, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Preparation of example 167 from the title compound of Example 151 (47 mg, 0.085 mmol) and 4M HCl in dioxane (10 mL) was carried out analogously to Example 91. Isolation, also in an analogous manner, included freebasing with triethylamine and subsequent silica gel chromatography eluting with 3:1:1 hexane:ethyl acetate:ethanol. With ice bath cooling, the purified freebase in CH2Cl2 (10 mL) was treated with 4M HCl in dioxane (0.1 mL). After removal of the volatile components, the title compound (20 mg, 0.041 mmol) was obtained as an orange/yellow powder in 48% yield.

Workup

  1. washeluting with 3:1:1 hexane
  2. temperatureWith ice bath cooling
  3. additionthe purified freebase in CH2Cl2 (10 mL) was treated with 4M HCl in dioxane (0.1 mL)
  4. customAfter removal of the volatile components

Sources & evidence

ORD record
ord-9cde8e6e3abe452c8b1d889559806841
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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