Acetic Acid → HCID 67176840, compound

HRID 1622044Notes

Reaction equation

HRID 1622044 reaction equation
COC1C=CC(C[O:8][C:9](=[O:68])[CH:10]([NH:25][C:26]([NH:28][CH:29]([C:56]([O:58]CC2C=CC(OC)=CC=2)=[O:57])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([C:37]2[CH:38]=[N:39][CH:40]=[C:41]([Sn](CCCC)(CCCC)CCCC)[CH:42]=2)=[O:36])=[O:27])[CH2:11][CH2:12][C:13]([O:15]CC2C=CC(OC)=CC=2)=[O:14])=CC=1.C(O)(=O)C.[I-:75].[Na+].ClN1C(=O)CCC1=O>CO>[C:56]([CH:29]([NH:28][C:26](=[O:27])[NH:25][CH:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:9]([OH:8])=[O:68])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([C:37]1[CH:38]=[N:39][CH:40]=[C:41]([I:75])[CH:42]=1)=[O:36])([OH:58])=[O:57]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 31398ChlorosuccinimideHCID 74399710HCID 74399710, compound

Product 1

HCID 67176840HCID 67176840, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7 (0.025 g, 0.023 mmol) in 2 mL methanol was added 0.020 mL acetic acid and sodium iodide (0.017 g, 0.113 mmol), followed by N-chlorosuccinimide (0.025 g, 0.187 mmol). After 20 min at room temperature, the solvent was removed under a stream of nitrogen. A solution of TFA in CH2Cl2 (1:1, 2 mL) was then added to the residue. After 1 h at room temperature, 8 (0.008 g, 62%) was isolated by HPLC (Econosphere C18 10μ., 250×10 mm, H2O/CH3CN/TFA (85/15/0.1), 4 mL/min, product peak eluting at 10 min). 1H NMR (400 MHz, D2O) δ 9.00-9.15 (m, 3H), 4.18-4.24 (m, 2H), 3.40-3.41 (m, 2H), 2.45-2.49 (m, 2H), 2.12-2.13 (m, 1H), 1.85-1.97 (m, 2H), 1.64-1.73 (m, 3H), 1.44 (m, 2H). ESI-Mass calcd for C18H24IN4O8 [M+H]+ 551.1. found 551.0. FAB-HRMS calcd for C18H24IN4O8 [M+H]+ 551.0639. found 551.0607.

Workup

  1. customthe solvent was removed under a stream of nitrogen
  2. additionA solution of TFA in CH2Cl2 (1:1, 2 mL) was then added to the residue
  3. waitAfter 1 h at room temperature

Sources & evidence

ORD record
ord-f56d88b1f9794536bfba2175495e0fc2
Source dataset
uspto-grants-2014_07
Patent number
US08778305B2

Reaction notes

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