Trifluoroacetic acid → HCID 69621723, compound

HRID 1245289Notes

Reaction equation

HRID 1245289 reaction equation
C(OC(=O)[NH:7][C:8]([C:11](=[O:45])[NH:12][CH:13]([C:23](=[O:44])[N:24]([CH2:27][C:28]1[C:29]([CH3:43])([CH3:42])[NH:30][S:31](=[O:41])(=[O:40])[C:32]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[CH2:25][CH3:26])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:10])[CH3:9])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:39].[NH2:7][C:8]([CH3:9])([CH3:10])[C:11]([NH:12][CH:13]([C:23](=[O:44])[N:24]([CH2:27][C:28]1[C:29]([CH3:43])([CH3:42])[NH:30][S:31](=[O:41])(=[O:40])[C:32]=1[C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)[CH2:25][CH3:26])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:45]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69621682HCID 69621682, compound

Product 1

HCID 69621723HCID 69621723, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound from above, [1-(2-benzyloxy-1-{[5-(4-chloro-phenyl)-3,3-dimethyl-1,1-dioxo-2,3-dihydro-1H-1λ6-isothiazol-4-ylmethyl]-ethyl-carbamoyl}-ethylcarbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (1.00 g, 1.48 mmol) was dissolved in dichloromethane (30 mL) and trifluoroacetic acid added (5 mL) and the mixture stirred for 2 hours at room temperature. The mixture was concentrated in vacuo and the residue treated with saturated aqueous sodium bicarbonate followed by extraction with ethyl acetate. The combined extracts were dried over sodium sulfate. Concentration left a residue which was chromatographed over silica (methanol/chloroform) to give the amine. This amine was dissolved in minimal ethyl acetate and treated with excess ether/hydrochloric acid. Concentration and drying netted 0.37 g (41%) of the desired hydrochloride salt as a white solid. Anal. Calc'd for C28H3ClN4O5S.1.1HCl: C, 54.49; H, 6.22; N, 9.38. Found: C, 54.17; H, 6.16; N, 9.38. m.p. 107–113° C. MS(ES): (M+1)+ 579.4 m/z.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue treated with saturated aqueous sodium bicarbonate
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. concentrationConcentration
  6. waitleft a residue which
  7. customwas chromatographed over silica (methanol/chloroform)

Sources & evidence

ORD record
ord-1e48a780e8ff425ab5fb35dfcd134442
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

Loading…