Dimethylformamide → carbamate Ara-C

HRID 842585Notes

Reaction equation

HRID 842585 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1[C:16]([NH2:17])=[N:15][C:13](=[O:14])[N:12]([C@@H:18]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:20]([OH:25])[C@@H:19]2[OH:26])[CH:11]=1.CN(C=[O:31])C>C(Cl)Cl>[C:18](=[O:22])([O-:31])[NH2:12].[CH:10]1[C:16]([NH2:17])=[N:15][C:13](=[O:14])[N:12]([C@@H:18]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:20]([OH:25])[C@@H:19]2[OH:26])[CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6253CytarabineHCID 81531Diisopropylethylamine

Product 1

HCID 131723190carbamate Ara-C

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIEA (60 μL, 0.35 mmol) is added to a mixture of SC-PEG 40 kDa (4, 1.0 g, 0.025 mmol) and 1 (0.15 g, 0.5 mmol) in DCM (10 mL) and DMF (10 mL) and the mixture is stirred overnight at room temperature. The solvent is removed in vacuo and the residue is recrystallized from IPA to give PEG-carbamate-Ara-C (5).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is recrystallized from IPA

Sources & evidence

ORD record
ord-e8c19122cbe44a9a9a84292849ae050c
Source dataset
uspto-grants-2002_04
Patent number
US06376470B1

Reaction notes

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