Water → HCID 21957039, compound

HRID 902945Notes

Reaction equation

HRID 902945 reaction equation
C(O)(C(F)(F)F)=O.O.C([O:13][C:14](=[O:46])[CH2:15][CH:16]([C:29](=[O:45])[N:30]([C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:35][CH:34]=1)[CH2:31][CH3:32])[CH:17]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([OH:20])=[O:19])(C)(C)C>C(Cl)Cl>[C:36]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:35]=[CH:34][C:33]([N:30]([CH2:31][CH3:32])[C:29]([CH:16]([CH2:15][C:14]([OH:46])=[O:13])[CH:17]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:18]([OH:20])=[O:19])=[O:45])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 69212306HCID 69212306, compound

Product 1

HCID 21957039HCID 21957039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of TFA (30%) in DCM (5 mL) containing water (5%) was added the compound of Example 55. The reaction mixture was stirred for 2 h at room temperature, after which time, the solvent was removed. The residue was triturated with ether and evaporated. The residue was partitioned between sodium hydroxide (1N) and ether. Following separation, the alkaline phase was acidified to pH 1 using HCl (1N) and extracted with ethyl acetate. The recombined organic layer was dried over sodium sulfate, filtered and evaporated. FAB: 460.1(MH+), FAB(M−H+):458.0.

Workup

  1. customafter which time, the solvent was removed
  2. customThe residue was triturated with ether
  3. customevaporated
  4. customThe residue was partitioned between sodium hydroxide (1N) and ether
  5. customseparation
  6. extractionextracted with ethyl acetate
  7. dry with materialThe recombined organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-11e758514dd8426982dfd10c67c548cf
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

Loading…