Trifluoroacetic acid methylene chloride → 3-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminobenzoic acid

HRID 1241968Notes

Reaction equation

HRID 1241968 reaction equation
C([O:5][C:6](=[O:40])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH3:15])=[C:9]([N:16]=[C:17]2[N:21]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:20](=[O:29])[C:19](=[C:30]3[N:34]([CH3:35])[C:33]4[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=4[S:31]3)[S:18]2)[CH:8]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH2:22]([N:21]1[C:20](=[O:29])[C:19](=[C:30]2[N:34]([CH3:35])[C:33]3[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=3[S:31]2)[S:18][C:17]1=[N:16][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[NH:13][CH2:14][CH3:15])[C:6]([OH:40])=[O:5])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 738550843-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminobenzoic acid tert-butyl ester

Product 1

HCID 738550123-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]-4-ethylaminobenzoic acid

Procedure

The product of Example 90 was treated with 55% TFA/DCM for 1 h, concentrated under reduced pressure, diluted with DCM, concentrated once again, diluted with DCM, allowed to stand over solid NaHCO3, filtered and concentrated to afford the title product. MS(ESI): 517 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with DCM
  3. concentrationconcentrated once again
  4. additiondiluted with DCM
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7df327a8355041ffac76e2588b3c77b4
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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