HCID 12072646, compound → HCID 11017897, compound

HRID 751753Notes

Reaction equation

HRID 751753 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:47]([O:49]CC(=O)C1C=CC=CC=1)=[O:48])[CH2:13][O:14][C:15]([C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:46])[C@@H:23]([NH:25][C:26]([C@@H:28]([N:30]([CH3:45])[C:31]([C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:32])[CH3:29])=[O:27])[CH3:24])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Zn].C(O)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:47]([OH:49])=[O:48])[CH2:13][O:14][C:15]([C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:46])[C@@H:23]([NH:25][C:26]([C@@H:28]([N:30]([CH3:45])[C:31]([C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])=[O:32])[CH3:29])=[O:27])[CH3:24])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 12072646HCID 12072646, compound

Product 1

HCID 11017897HCID 11017897, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

Under argon, are introduced into a solution of 17.0 g (21.0 mmol) of the compound from example 8A in 90 pc. aqueous acetic acid and 10.3 g (158 mmol) of zinc. The reaction mixture warms slightly and is cooled to 25° C. It is stirred at this temperature for 3 h and the mixture is subsequently filtered off with suction through kieselguhr and washed with ethyl acetate. The solvent is removed on a rotary evaporator, and the residue is taken up in ethyl acetate and extracted by shaking twice with 1N aqueous hydrochloric acid. The organic phase is concentrated again, treated three times with toluene and evaporated to dryness in vacuo and finally dried in vacuo. 14 g (94% of theory) are isolated. The product is reacted without further purification.

Workup

  1. filtrationthe mixture is subsequently filtered off with suction through kieselguhr
  2. washwashed with ethyl acetate
  3. customThe solvent is removed on a rotary evaporator
  4. extractionextracted
  5. stirringby shaking twice with 1N aqueous hydrochloric acid
  6. concentrationThe organic phase is concentrated again
  7. additiontreated three times with toluene
  8. customevaporated to dryness in vacuo
  9. customfinally dried in vacuo
  10. custom14 g (94% of theory) are isolated
  11. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-af7e1f2432cc4b759de8d411adf72c44
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Reaction notes

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