Hydrochloric Acid → HCID 67017287, compound

HRID 1024105Notes

Reaction equation

HRID 1024105 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][C:15](Br)([Br:18])[C@@H:14]2[C:20]2[CH:25]=[CH:24][C:23]([CH:26]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:8][CH:9]=1)=[O:4].C(N=C(N(C)C)N(C)C)(C)(C)C.Cl>ClCCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][C:15]([Br:18])=[C:14]2[C:20]2[CH:21]=[CH:22][C:23]([CH:26]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:24][CH:25]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 67017257HCID 67017257, compound

Product 1

HCID 67017287HCID 67017287, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of dibromide 3 (52 mg, 0.074 mmol) and 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG, 0.8 mL) in 1,2-dichloroethane (2 mL) was stirred at room temperature. After 3 days, 1 M HCl was added and the mixture was extracted with CH2Cl2 (3×25 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (0%→20% ethyl acetate/hexanes) gave the title compound contaminated with 15% of the alkene regioisomer 5b as an inseparable mixture (45 mg, 97%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe combined dichloromethane solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (0%→20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6b20ccae21d345e0a81e4823674ec8bd
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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