Chlorambucil → HCID 131721370, compound

HRID 618468Notes

Reaction equation

HRID 618468 reaction equation
[CH:1]1[C:6]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=[C:3]([N:13]([CH2:17][CH2:18][Cl:19])[CH2:14][CH2:15][Cl:16])[CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:35][CH2:36][C:37]([OH:39])=[O:38].[CH2:40]([OH:47])[C:41]([NH2:46])([CH2:44][OH:45])[CH2:42][OH:43].[CH3:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][C:63]([O:65][CH2:66][CH:67]([O:87][C:88]([CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH3:104])=[O:89])[CH2:68][O:69][C:70]([CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])=[O:71])=[O:64]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:5]1[C:6]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:1][CH:2]=[C:3]([N:13]([CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18][Cl:19])[CH:4]=1.[NH2:35][CH2:36][C:37]([OH:39])=[O:38].[CH2:40]([OH:47])[C:41]([NH2:46])([CH2:44][OH:45])[CH2:42][OH:43].[CH3:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][C:63]([O:65][CH2:66][CH:67]([O:87][C:88]([CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH3:104])=[O:89])[CH2:68][O:69][C:70]([CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86])=[O:71])=[O:64]

Participants

6

Reactant 3

HCID 2708ChlorambucilHCID 10868DicyclohexylcarbodiimideHCID 131721371HCID 131721371, compound

Product 1

HCID 131721370HCID 131721370, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of chlorambucil (0.240 g, 0.789 mmol) in DCM (16 ml) at 0° C. was added DCC (0.171 g, 0.828 mmol) and DMAP (0.005 g, 0.039 mmol), followed by the Gly-Tris-Tripalmitate (0.740 g, 0.828 mmol). The resulting mixture was stirred at room temperature overnight. The precipitate was filtered and the filtrate washed with 5% acetic acid aqueous solution, then H2O three times until the pH was 7. The organic phase was dried (MgSO4), then concentrated in vacuo. The crude product was purified by the flash chromatography (30%, 40% ethyl acetate/hexane), then recrystallized from ethyl acetate/hexane to give the title compound (0.45 g) as a white solid in 48.2% yield.

Workup

  1. filtrationThe precipitate was filtered
  2. washthe filtrate washed with 5% acetic acid aqueous solution
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by the flash chromatography (30%, 40% ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0514de94d9d94eac8af786b768bff35d
Source dataset
uspto-grants-1999_09
Patent number
US05952499

Reaction notes

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