Dichloromethane → HCID 10141610, compound

HRID 1375072Notes

Reaction equation

HRID 1375072 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:40])[CH2:21][C:22]3[CH:38]=[C:37]([CH3:39])[C:25]4[N:26]=[C:27]([NH:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[CH3:36])[O:28][C:24]=4[CH:23]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.ClCCl>O>[CH3:39][C:37]1[C:25]2[N:26]=[C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])[O:28][C:24]=2[CH:23]=[C:22]([CH2:21][C:20]([NH:19][C:16]2[CH:15]=[CH:14][C:13]([C:8]3([CH2:7][C:6]([OH:41])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:18][CH:17]=2)=[O:40])[CH:38]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69419366HCID 69419366, compound

Product 1

HCID 10141610HCID 10141610, compoundYield 428%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[1-{4-[2-[4-Methyl-2-o-tolylamino-benzoxazol-6-yl]-acetylamino]-phenyl}-cyclopentyl]-acetic acid tert-butyl ester [0.065 g, Reference Example 1(d)] was treated with a mixture of trifluoroacetic acid (2.2 mL), dichloromethane (0.5 mL) and water (0.25 mL). The resultant solution was stirred at room temperature, under argon, for 1.5 hours and then the colourless solution was evaporated. The residue was chased twice with toluene (15 mL) to yield a clear gum. This gum was triturated with pentane and the solid obtained was washed with pentane and then dried at 60° C., under vacuum, to give the title compound (0.25 g) as an off-white solid, m.p. softens at 110° C. then slowly melts from 120–150° C.

Workup

  1. customthe colourless solution was evaporated
  2. customto yield a clear gum
  3. customThis gum was triturated with pentane
  4. customthe solid obtained
  5. washwas washed with pentane
  6. customdried at 60° C., under vacuum

Sources & evidence

ORD record
ord-5a6fafa7c8104e5cb2e160b98d271659
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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