Trifluoroacetic acid → HCID 18465676, compound

HRID 2230447Notes

Reaction equation

HRID 2230447 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([NH:16][CH:17]1[C:23](=[O:24])[N:22]2[CH:25]([C:29]([NH:31][CH:32]([C:41](=[O:54])[CH2:42][O:43][C:44](=[O:53])[C:45]3[C:50]([Cl:51])=[CH:49][CH:48]=[CH:47][C:46]=3[Cl:52])[CH2:33][C:34]([O:36]C(C)(C)C)=[O:35])=[O:30])[CH2:26][CH2:27][CH2:28][N:21]2[C:20](=[O:55])[CH2:19][CH2:18]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8]([NH:16][CH:17]1[C:23](=[O:24])[N:22]2[CH:25]([C:29]([NH:31][CH:32]([C:41](=[O:54])[CH2:42][O:43][C:44](=[O:53])[C:45]3[C:50]([Cl:51])=[CH:49][CH:48]=[CH:47][C:46]=3[Cl:52])[CH2:33][C:34]([OH:36])=[O:35])=[O:30])[CH2:26][CH2:27][CH2:28][N:21]2[C:20](=[O:55])[CH2:19][CH2:18]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18465818HCID 18465818, compound

Product 1

HCID 18465676HCID 18465676, compoundYield 98%

Conditions

Temperature
0 °C

Procedure

TFA (25 ml) was added dropwise to an ice cold stirred solution of the ester 216e (2.11 g, 3.0 mmol). The mixture was stirred at 0° C. for 20 min then at room temperature for 1 h. The mixture was evaporated to dryness then coevaporated with ether three times. Addition of dry ether (50 ml) and filtration afforded 1.9 g (98%) of 217e as a colourless solid: mp 126-130° C.; [α]D30 −122.0 (c 0.1, MeOH); IR (KBr) 3322, 1740, 1658, 1651, 1532, 1433, 1277, 1150; 1H NMR (D6-DMSO) δ8.87 (1H, d, J=7.4), 8.61 (1H, d, J=7.8), 7.92-7.86 (2H, m), 7.65-7.43 (6H, m), 5.25-5.12 (3H, m), 4.94-4.60 (2H, m), 4.44-4.22 (1H, m), 3.43-3.10 (1H, m), 3.00-2.52 (3H, m), 2.45-2.10 (3H, m), 2.10-1.75 (2H, m), 1.75-1.50 (2H, m); Anal. Calcd for C29H28Cl2N4O9.1H2O: C, 52.34; H, 4.54; N, 8.42; Cl, 10.66. Found: C, 52.02; H, 4.36; N, 8.12; Cl, 10.36. MS (ES−) 649/7/5 (M−1), 411 (100%).

Workup

  1. waitat room temperature for 1 h
  2. customThe mixture was evaporated to dryness
  3. additionAddition of dry ether (50 ml) and filtration

Sources & evidence

ORD record
ord-806ed1b7ce774947a83246da1675def7
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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