Stearoyl chloride → HCID 88120683, compound

HRID 480542Notes

Reaction equation

HRID 480542 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:21][C:22]([O:25][C:26](=[O:72])[C@H:27]([CH2:67][CH2:68][CH2:69][CH2:70][NH2:71])[N:28]([CH2:48][CH2:49][N:50]([CH2:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:29][CH2:30][N:31]([CH2:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:24])[CH3:23]>C(Cl)(Cl)Cl>[CH3:24][C:22]([O:25][C:26](=[O:72])[C@H:27]([CH2:67][CH2:68][CH2:69][CH2:70][NH:71][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:28]([CH2:29][CH2:30][N:31]([CH2:40][C:41]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:47])[CH2:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:48][CH2:49][N:50]([CH2:51][C:52](=[O:58])[O:53][C:54]([CH3:55])([CH3:56])[CH3:57])[CH2:59][C:60](=[O:61])[O:62][C:63]([CH3:64])([CH3:65])[CH3:66])([CH3:21])[CH3:23]

Participants

4

Reactant 2

HCID 8212Stearoyl chlorideHCID 11679335HCID 11679335, compound

Product 1

HCID 88120683HCID 88120683, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Stearoyl chloride (5.45 g; 18 mmol) dissolved in CHCl3 (60 mL) was added dropwise in 1 h to a solution of N2,N2-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-L-lysine 1,1-dimethylethyl ester (13.5 g; 18 mmol) in CHCl3 (300 mL) at 0° C. After 10 min the reaction mixture was allowed to rise to room temperature and TLC analysis showed the complete conversion of the starting materials. The solution was washed with 5% aq. NaHCO3, the organic phase was separated, dried over Na2SO4 and then evaporated under reduced pressure. The crude product was purified by flash chromatography (n-hexane/EtOAc=6/4 (v/v)) to give the desired product (11.3 g; 11.2 mmol). Yield 62%. HPLC: 95% (area %). the 13C-NMR, MS and IR spectra were consistent with the structure.

Workup

  1. customto rise to room temperature
  2. washThe solution was washed with 5% aq. NaHCO3
  3. customthe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by flash chromatography (n-hexane/EtOAc=6/4 (v/v))

Sources & evidence

ORD record
ord-821265a6ab284c16b5c761cb783c1a7f
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Reaction notes

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