HCID 86747858, compound → HCID 67798175, compound

HRID 1077957Notes

Reaction equation

HRID 1077957 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-031ad47552b34cc39add3dc228a56a11
Source dataset
uspto-grants-1996_08
Patent number
US05545662

Reaction notes

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