Trifluoroacetic acid → HCID 57500374, compound

HRID 2273542Notes

Reaction equation

HRID 2273542 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:60]=[CH:61][CH:62]=1)[C:22]([NH:24][C:25]1[C:26]([CH3:59])=[C:27]([C:34]([C:36]2[CH:37]=[CH:38][C:39]([NH:52][C:53](=[O:58])[C:54]([F:57])([F:56])[F:55])=[C:40]([CH:51]=2)[C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])=[O:35])[N:28]2[C:33]=1[CH:32]=[CH:31][CH:30]=[CH:29]2)=[O:23])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:60]=[CH:61][CH:62]=1)[C:22]([NH:24][C:25]1[C:26]([CH3:59])=[C:27]([C:34]([C:36]2[CH:37]=[CH:38][C:39]([NH:52][C:53](=[O:58])[C:54]([F:55])([F:56])[F:57])=[C:40]([CH:51]=2)[C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])=[O:35])[N:28]2[C:33]=1[CH:32]=[CH:31][CH:30]=[CH:29]2)=[O:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57500372HCID 57500372, compound

Product 1

HCID 57500374HCID 57500374, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16 ml (0.20 mol) of trifluoroacetic acid are added to the suspension of 6.28 g (8.28 mmol) of benzyl 5-({1-[(3-{2-[(tert-butoxycarbonyl)amino]ethoxy}benzoyl)-amino]-2-methylindolizin-3-yl}carbonyl)-2-[(trifluoroacetyl)amino]benzoate in 40 ml of dichloromethane. After stirring at ambient temperature for 30 minutes, the reaction medium is poured into 1 l of a saturated aqueous solution of sodium bicarbonate. The precipitate is filtered, washed thoroughly with water and then with diisopropyl ether and dried, so as to obtain 4.5 g (82%) of a yellow powder.

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed thoroughly with water
  3. dry with materialwith diisopropyl ether and dried

Sources & evidence

ORD record
ord-c12251f89c85436fb72e7a61e8d12974
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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