HCID 178472449, compound → HCID 178472450, compound

HRID 1087972Notes

Reaction equation

HRID 1087972 reaction equation
C([O:5][C:6](=[O:52])[CH:7]([CH:28]([C:30](=[O:51])[C@H:31]([CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[NH:32][C:33](=[O:35])[CH3:34])[NH2:29])[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[C:33]([NH:32][C@H:31]([C:30]([CH:28]([NH2:29])[CH:7]([CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:6]([OH:52])=[O:5])=[O:51])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])(=[O:35])[CH3:34]

Participants

4

Reactant 1

HCID 178472449HCID 178472449, compound

Product 1

HCID 178472450HCID 178472450, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The t-butyl ester from Example 1 (571 mg, 0.783 mmol) was dissolved in a mixture of trifluoroacetic acid (2 ml) and dichloromethane (1 ml). The solution was kept at 4° C. overnight, then concentrated to dryness under vacuum, and the residue was azeotroped six times with dichloromethane. The resulting crude product was then taken up in ethyl acetate and washed with water until the washings were neutral. The organic phase was dried (MgSO4) and evaporated under vacuum to afford the title compound (442 mg, 84%) as a white foam. Found: C,61.89; H,7.76; N,7.93. C35H52N4O9 (0.5 H2O) requires C,61.65; H,7.69; N,8.22%.

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. customthe residue was azeotroped six times with dichloromethane
  3. washwashed with water until the washings
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-6c84f8cdccd545919f4e3a985c54b87b
Source dataset
uspto-grants-1990_10
Patent number
US04960792

Reaction notes

Loading…