Triethylamine → HCID 68295985, compound

HRID 589979Notes

Reaction equation

HRID 589979 reaction equation
F[C:2](F)(F)[CH2:3][CH2:4][C:5]([N:7]([CH3:28])[S:8]([N:11]1[C:16]2([CH2:18][CH2:17]2)[CH2:15][N:14]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9])=[O:6].[CH:31]1(C(Cl)=O)CCC[CH2:32]1.CCN(CC)CC.O=S1(=O)CCC(C(Cl)=O)C1>C(Cl)Cl>[CH3:28][N:7]([S:8]([N:11]1[C:16]2([CH2:18][CH2:17]2)[CH2:15][N:14]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9])[C:5]([CH:4]1[CH2:32][CH2:31][CH2:2][CH2:3]1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 450815271,1-Dioxo-1lambda~6~-thiolane-3-carbonyl chlorideHCID 86706434HCID 86706434, compound

Product 1

HCID 68295985HCID 68295985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 4 (0.071 mmol) was dissolved in dry DCM (1 mL) and added commercial available cyclopentanecarbonyl chloride (0.085 mmol) and Et3N (0.21 mmol). Stirred at rt for 1 h and then at 40° C. for 1.5 h. More 1,1-dioxothiolane-3-carbonyl chloride was added (2×0.107 mmol) with 1 h in between each portion. After being stirred at 40° C. for 1 h the reaction mixture was concentrated in vacuo, added 2,2,2-trifluoroethanol (1 mL) and stirred at 60° C. for 16 h. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. waitat 40° C. for 1.5 h
  2. stirringAfter being stirred at 40° C. for 1 h the reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionadded 2,2,2-trifluoroethanol (1 mL)
  5. stirringstirred at 60° C. for 16 h
  6. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-fe2cc12682cb4767a49720e3259d3f5a
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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