Dicyclohexylcarbodiimide → t-Boc-Glycine Irinotecan

HRID 19430

Reaction equation

HRID 19430 reaction equation
[CH3:1][CH2:2][C:3]1[C:12]2[CH2:13][N:14]3[C:19](=[O:20])[C:18]4[CH2:21][O:22][C:23]([C@:25]([OH:28])([CH2:26][CH3:27])[C:17]=4[CH:16]=[C:15]3[C:11]=2[N:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:34][CH2:33]1)=[O:31])[CH:7]=[CH:8]2)=[O:24].[CH3:44][C:45]([O:48][C:49]([NH:51][CH2:52][C:53]([OH:55])=[O:54])=[O:50])([CH3:47])[CH3:46].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:47][C:45]([O:48][C:49]([NH:51][CH2:52][C:53]([OH:55])=[O:54])=[O:50])([CH3:44])[CH3:46].[CH3:1][CH2:2][C:3]1[C:12]2[CH2:13][N:14]3[C:19](=[O:20])[C:18]4[CH2:21][O:22][C:23]([C@:25]([OH:28])([CH2:26][CH3:27])[C:17]=4[CH:16]=[C:15]3[C:11]=2[N:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([O:29][C:30]([N:32]1[CH2:33][CH2:34][CH:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:36][CH2:37]1)=[O:31])[CH:7]=[CH:8]2)=[O:24]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 60838IrinotecanHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 131728194t-Boc-Glycine Irinotecan

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a flask, 0.1 g Irinotecan (0.1704 mmoles), 0.059 g t-Boc-Glycine (0.3408 mmoles), and 0.021 g DMAP (0.1704 mmoles) were dissolved in 13 mL of anhydrous dichloromethane (DCM). To the solution was added 0.070 g DCC (0.3408 mmoles) dissolved in 2 mL of anhydrous DCM. The solution was stirred overnight at room temperature. The solid was removed through a coarse frit, and the solution was washed with 10 mL of 0.1N HCL in a separatory funnel. The organic phase was further washed with 10 mL of deionized H2O in a separatory funnel and then dried with Na2SO4. The solvent was removed using rotary evaporation and the product was further dried under vacuum. 1H NMR (DMSO): δ 0.919 (t, CH2CH3), 1.34 (s, C(CH3)3), 3.83 (m, CH2), 7.66 (d, aromatic H).

Workup

  1. customThe solid was removed through a coarse frit
  2. washthe solution was washed with 10 mL of 0.1N HCL in a separatory funnel
  3. washThe organic phase was further washed with 10 mL of deionized H2O in a separatory funnel
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed
  6. customevaporation
  7. customthe product was further dried under vacuum

Sources & evidence

ORD record
ord-86ad3ea06bfd4927a9b6bd35228aecdf
Source dataset
uspto-grants-2010_06
Patent number
US07744861B2

Linked notes

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