Diethyl Ether → HCID 57500378, compound

HRID 2273544Notes

Reaction equation

HRID 2273544 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:60])[CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:57]=[CH:58][CH:59]=1)[C:19]([NH:21][C:22]1[C:23]([CH3:56])=[C:24]([C:31]([C:33]2[CH:34]=[CH:35][C:36]([NH:49][C:50](=[O:55])[C:51]([F:54])([F:53])[F:52])=[C:37]([CH:48]=2)[C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])=[O:32])[N:25]2[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]2)=[O:20])(C)(C)C.C(OCC)C>ClCCl>[CH2:41]([O:40][C:38]([C:37]1[CH:48]=[C:33]([CH:34]=[CH:35][C:36]=1[NH:49][C:50](=[O:55])[C:51]([F:54])([F:53])[F:52])[C:31]([C:24]1[N:25]2[C:30]([CH:29]=[CH:28][CH:27]=[CH:26]2)=[C:22]([NH:21][C:19]([C:18]2[CH:17]=[C:16]([CH:59]=[CH:58][CH:57]=2)[O:15][CH2:14][C:13]([OH:60])=[O:12])=[O:20])[C:23]=1[CH3:56])=[O:32])=[O:39])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 57500377HCID 57500377, compound

Product 1

HCID 57500378HCID 57500378, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17 ml (0.22 mol) of trifluoroacetic acid are added to the suspension of 7.95 g (10.9 mmol) of benzyl 5-[(1-{[3-(2-tert-butoxy-2-oxoethoxy)benzoyl]amino}-2-methylindolizin-3-yl)carbonyl]-2-[(trifluoroacetyl)amino]benzoate in 55 ml of dichloromethane at ambient temperature. The mixture becomes rapidly homogenized. The solution is stirred for 3 hours and concentrated to dryness. The solid obtained is taken up with ethyl ether, filtered and dried. 7.25 g (99%) of an orange powder are obtained.

Workup

  1. stirringThe solution is stirred for 3 hours
  2. concentrationconcentrated to dryness
  3. customThe solid obtained
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-a69126707c5942d2b2bf84cbce3dd1fa
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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