Dichloromethane → HCID 18932923, compound

HRID 1597826Notes

Reaction equation

HRID 1597826 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:14]([CH3:16])[CH3:15])=[O:11])[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:4][CH:3]=1.C([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])C.Cl[C:40](Cl)([O:42][C:43](=[O:49])OC(Cl)(Cl)Cl)Cl.Cl[CH2:52]Cl>>[O:8]=[C:7]1[N:6]([CH2:9][C:10]([NH:12][CH:13]([B:17]2[O:21][C:20]([CH3:22])([CH3:23])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:14]([CH3:16])[CH3:15])=[O:11])[C:5]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:4][CH:3]=[C:2]1[NH:1][C:43]([O:42][CH2:40][C:52]1[CH:36]=[CH:35][N:34]=[CH:37][CH:38]=1)=[O:49]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 94429TriphosgeneHCID 18932915HCID 18932915, compound

Product 1

HCID 18932923HCID 18932923, compound

Procedure

A solution of the product from Example 2 (0.50 g) and triethylamine (0.80 mL) in dichloromethane (5 mL) was cooled with an ice-water bath. To the solution was added triphosgene (0.17 g) in dichloromethane (1 mL) over 2 minutes. A dichloromethane (1 mL) wash of the addition syringe was also added to the reaction mixture. The mixture was stirred at ice bath temperature for 30 minutes. Solid 4-pyridinemethanol (0.38 g) was added in a single portion to the mixture. Stirring was continued at ice bath temperature for 90 minutes, and the solution was allowed to warm to room temperature overnight. The mixture was diluted with dichloromethane, washed (water), dried and evaporated to a brown foam (0.60 g). This material was purified by chromatography, with chloroform:methanol (50:1) as the eluent, to give the title compound (0.11 g) as a yellow solid; TLC: Rf =0.35, methanol:chloroform (5:95); NMR: 0.85 (d,6, J=7), 1.17 (s,1), 1.17-1.80 (m, 1), 2.68 (t,1), 4.48 (s,2), 5.24 (s,2), 7.44-7.56 (m,7), 8.28 (d,1, J=5.5), 8.47 (s,1), 8.58 (dd,2), 9.23 (s,1); MS: m/z=562(M+1).

Workup

  1. washA dichloromethane (1 mL) wash of the addition syringe
  2. additionwas also added to the reaction mixture
  3. additionSolid 4-pyridinemethanol (0.38 g) was added in a single portion to the mixture
  4. stirringStirring
  5. customwas continued at ice bath
  6. waittemperature for 90 minutes
  7. additionThe mixture was diluted with dichloromethane
  8. washwashed (water)
  9. customdried
  10. customevaporated to a brown foam (0.60 g)
  11. customThis material was purified by chromatography, with chloroform:methanol (50:1) as the eluent

Sources & evidence

ORD record
ord-598663bcdc7e458d88047c6a5518b162
Source dataset
uspto-grants-1998_04
Patent number
US05736535

Reaction notes

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