HCID 69686765, compound → HCID 54417419, compound

HRID 1018321Notes

Reaction equation

HRID 1018321 reaction equation
C(OC([N:8]1[C:12]([CH2:13][CH2:14][C:15]23[CH2:24][CH:19]4[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]4)[CH2:16]2)[CH2:22]3)=[C:11]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])[CH:30]=2)=[O:27])[N:10]=[C:9]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH3:51])=O)(C)(C)C>FC(F)(F)C(O)=O>[CH2:38]([O:37][C:35](=[O:36])[C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([NH:28][C:26]([NH:25][C:11]2[N:10]=[C:9]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[CH3:51])[NH:8][C:12]=2[CH2:13][CH2:14][C:15]23[CH2:24][CH:19]4[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]4)[CH2:16]2)[CH2:22]3)=[O:27])[CH:30]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

3

Reactant 1

HCID 69686765HCID 69686765, compound

Product 1

HCID 54417419HCID 54417419, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The product of step d (237 mg, 0.34 mmol) was dissolved in trifluoroacetic acid (2 ml) and the solution was stirred at room temperature for 1 h. The trifluroracetic acid was removed in vacuo. The residue was partitioned between DCM and saturated aqueous sodium hydrogen carbonate. The organic layer was dried (MgSO4) and the solvent was evaporated to afford the product as a white solid (190 mg, 94%). 1H NMR (300 MHz, CDCl3) 10.84 (1H, br s), 8.96 (1H, br s), 8.08 (1H, s), 7.75 (1H, d), 7.52 (1H, d), 7.47-7.27 (1OH, m), 6.86 (1H, s), 5.36 (2H, s), 2.65 (3H, s), 2.57 (2H, m), 1.95 (3H, br s), 1.65 (6H, m), 1.51 (6H, s), 1.37 (2H, m).

Workup

  1. customThe trifluroracetic acid was removed in vacuo
  2. customThe residue was partitioned between DCM and saturated aqueous sodium hydrogen carbonate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9a0058ec9a004a86a92ff039b2d93d14
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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