Cyclopentane-1,3-diol → HCID 68576199, compound

HRID 1865302Notes

Reaction equation

HRID 1865302 reaction equation
Cl.[O:2]1CCO[CH2:4][CH2:3]1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:22][CH2:23][N:24]2[CH2:31][CH:30]3[CH:26]([CH2:27][N:28]([C:32]([C:34]4[C:35]([CH3:41])=[N:36][CH:37]=[N:38][C:39]=4[CH3:40])=[O:33])[CH2:29]3)[CH2:25]2)[CH2:17][CH2:16]1)=[O:14])(C)([CH3:10])[CH3:9].C1(O)CCC(O)C1>CC#N>[OH:2][CH:3]1[CH2:4][CH2:10][CH:8]([O:12][C:13]([N:15]2[CH2:20][CH2:19][CH:18]([CH:21]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:22][CH2:23][N:24]3[CH2:31][CH:30]4[CH:26]([CH2:27][N:28]([C:32]([C:34]5[C:35]([CH3:41])=[N:36][CH:37]=[N:38][C:39]=5[CH3:40])=[O:33])[CH2:29]4)[CH2:25]3)[CH2:17][CH2:16]2)=[O:14])[CH2:9]1

Participants

5

Reactant 3

HCID 100165Cyclopentane-1,3-diolHCID 204431481,4-Dioxane hydrochlorideHCID 68584820HCID 68584820, compound

Product 1

HCID 68576199HCID 68576199, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of HCl-dioxane (1 mL, 4.0 M) and 78a (35 mg, 0.064 mmol) was stirred at RT for 90 min. The solvent was removed, and the residue was dried in vacuo. Cyclopentane-1,3-diol (cis/trans, 9 μL, 0.096 mmol) was added to a solution of N,N′-disuccimidylcarbonate (30 mg, 0.12 mmol) and TEA (44 μL, 0.32 mmol) in MeCN (0.47 mL) and the solution was stirred for 4 h. A solution of the above residue from the Boc deprotection in MeCN was added and the reaction mixture was stirred for 3 h. The solvent was evaporated and the crude product was purified on a preparative TLC plate developed with a mixture of 45% DCM and 55% of DCM/MeOH/NH4OH (60/10/1) to afford 0.011 g (30%) of V-6.

Workup

  1. customThe solvent was removed
  2. customthe residue was dried in vacuo
  3. stirringthe reaction mixture was stirred for 3 h
  4. customThe solvent was evaporated
  5. customthe crude product was purified on a preparative TLC plate
  6. additiondeveloped with a mixture of 45% DCM and 55% of DCM/MeOH/NH4OH (60/10/1)
  7. customto afford 0.011 g (30%) of V-6

Sources & evidence

ORD record
ord-37900ffdeb4642b29c843bab52798219
Source dataset
uspto-grants-2009_12
Patent number
US07625905B2

Reaction notes

Loading…