Water → HCID 59410227, compound

HRID 391753Notes

Reaction equation

HRID 391753 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1[C:22](=[O:51])[N:23]([C:27]2[C:32]([CH3:33])=[CH:31][C:30]([NH:34][CH2:35][C@@H:36]([OH:49])[CH2:37][N:38]3[C:46](=[O:47])[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:39]3=[O:48])=[CH:29][C:28]=2[CH3:50])[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:52](N1C=CN=C1)(N1C=CN=C1)=[O:53].O.ClCCl>C1(C)C=CC=CC=1>[Si:1]([O:18][CH2:19][CH2:20][C:21]1[C:22](=[O:51])[N:23]([C:27]2[C:28]([CH3:50])=[CH:29][C:30]([N:34]3[CH2:35][C@H:36]([CH2:37][N:38]4[C:46](=[O:47])[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[C:39]4=[O:48])[O:49][C:52]3=[O:53])=[CH:31][C:32]=2[CH3:33])[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 59410192HCID 59410192, compound

Product 1

HCID 59410227HCID 59410227, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

190 g (204 mmol) of the compound from Example 66A are dissolved in 1.01 l of toluene. 66.0 g (407 mmol) of 1,1′-carbonyldiimidazole are then added, and the mixture is heated at reflux for one hour. The mixture is then cooled to room temperature, and water and dichloromethane are added. The phases are separated and the organic phase is dried over sodium sulphate. After filtration, the mixture is evaporated to dryness under reduced pressure. The residue is triturated with methanol, and the solid which remains is filtered off and washed with methanol. This gives 130 g (87% of theory) of the desired product.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for one hour
  3. customThe phases are separated
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. filtrationAfter filtration
  6. customthe mixture is evaporated to dryness under reduced pressure
  7. customThe residue is triturated with methanol
  8. filtrationthe solid which remains is filtered off
  9. washwashed with methanol

Sources & evidence

ORD record
ord-958d16bf94244f51b793b36bc1625152
Source dataset
uspto-grants-2013_02
Patent number
US08383822B2

Reaction notes

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