HCID 86747858, compound → HCID 67798175, compound

HRID 1033782Notes

Reaction equation

HRID 1033782 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 δ1.39 (d, 3H) and 1.20-1.70 (overlapping m, 4H), 1.82 (br s, 2H), 3.23 (br s, variable, 2H), 3.33 (br s, 1H), 4.39 (m, 1H), 4.47 (apparent quintet, 1H), 5.03-5.13 (m, 6H), 5.27 (br d, 1H), 7.35 (m, 15H), 7.95 (br d, 1H); 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-afb5aaa47b734cba86b72067ed8d5fb8
Source dataset
uspto-grants-1994_05
Patent number
US05312831

Reaction notes

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