HCID 59737356, compound → HCID 59737289, compound

HRID 1907770Notes

Reaction equation

HRID 1907770 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:45]=[CH:44][C:20]([C:21]([NH:23][C:24]3[CH:25]=[C:26]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:27]=[CH:28][C:29]=3[NH:30]C(=O)OC(C)(C)C)=[O:22])=[CH:19][CH:18]=2)[CH2:13]1)(C(C)(C)C)(C)C>C(O)(C(F)(F)F)=O.O.CCOC(C)=O>[NH2:30][C:29]1[CH:28]=[CH:27][C:26]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[CH:25][C:24]=1[NH:23][C:21](=[O:22])[C:20]1[CH:44]=[CH:45][C:17]([N:14]2[CH2:15][CH2:16][C@H:12]([NH:11][CH2:10][CH2:9][OH:8])[CH2:13]2)=[CH:18][CH:19]=1

Participants

5

Reactant 1

HCID 59737356HCID 59737356, compound

Product 1

HCID 59737289HCID 59737289, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 443 (0.13 g, 0.206 mmol) in TFA (0.392 mL) and water (0.021 mL) was stirred for 2 h at room temperature. The solvent was evaporated and the residue obtained was dissolved in EtOAc, washed with sat NaHCO3 and sat NaCl. The organic layer was dried with MgSO4, filtered and concentrated to a brown solid. Trituration in Et2O generated the title compound 444 as a beige powder (70 mg, 82% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue obtained
  3. washwashed
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a brown solid

Sources & evidence

ORD record
ord-e6f2371358c741ffbd3d1df519d9400c
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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