HCID 86747858, compound → HCID 67798175, compound

HRID 1781339Notes

Reaction equation

HRID 1781339 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:49])[C@@H:10]([CH3:48])[NH:11][C:12](=[O:47])[C@@H:13]([CH2:22][CH2:23][CH2:24][CH:25]([C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[NH:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[NH:14]C(OC(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O>[C:1]1([CH2:7][O:8][C:9](=[O:49])[C@@H:10]([CH3:48])[NH:11][C:12](=[O:47])[C@@H:13]([CH2:22][CH2:23][CH2:24][CH:25]([C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[NH:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 86747858HCID 86747858, compound

Product 1

HCID 67798175HCID 67798175, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 40b (251 mg, 0.37 mmol) in TFA (870 μl) is stirred for 30 min at 0° C. The TFA is removed and the oil is taken up in EtOAc and washed with saturated NaHCO3 solution. Drying and removal of the solvent gives 3b (225 mg, slight excess) which is used in subsequent reactions without further handling: NMR δ 1.39 (d, 3 H) and 1.20-1.70 (overlapping m, 4 H), 1.82 (br s, 2 H), 3.23 (br s, variable, 2 H), 3.33 (br s, 1 H), 4.39 (m, 1 H), 4.47 (apparent quintet, 1 H), 5.03-5.13 (m, 6 H), 5.27 (br d, 1 H), 7.35 (m, 15 H), 7.95 (br d, 1 H); MS (FAB) m/z 576 (M+H), 598 (M+Na).

Workup

  1. customThe TFA is removed
  2. washwashed with saturated NaHCO3 solution
  3. customDrying
  4. customremoval of the solvent

Sources & evidence

ORD record
ord-a7bbe3157e2343b29b5ae2259a7f0280
Source dataset
uspto-grants-1997_05
Patent number
US05633280

Reaction notes

Loading…