Hydrochloric Acid → HCID 67017297, compound

HRID 1024106Notes

Reaction equation

HRID 1024106 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](Cl)([Cl: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]([Cl: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 59815128HCID 59815128, compound

Product 1

HCID 67017297HCID 67017297, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of dichloride 4 (12 mg, 0.019 mmol) and 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG, 0.2 mL) in 1,2-dichloroethane (0.5 mL) was stirred at 60° C. After 70 h, 1 M HCl (28 mL) was added and the mixture was extracted with 20 mL CH2Cl2. The dichloromethane solution was washed further with 1 M HCl (3×25 mL) and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (0%→15% ethyl acetate/hexanes) gave the title compound, contaminated with 15% of the alkene regioisomer 6b as an inseparable mixture (10 mg, 93%).

Workup

  1. extractionthe mixture was extracted with 20 mL CH2Cl2
  2. washThe dichloromethane solution was washed further with 1 M HCl (3×25 mL)
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (0%→15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0a7862a9a2e441e09eed7f796075d6b5
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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