Methanol → HCID 10279422, compound

HRID 1375066Notes

Reaction equation

HRID 1375066 reaction equation
C([O:5][C:6](=[O:42])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:41])[CH2:21][C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[CH3:38])=[O:30])=[C:24]([O:39][CH3:40])[CH:23]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)(C)(C)C.ClCCl.O.CO>FC(F)(F)C(O)=O>[CH3:40][O:39][C:24]1[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:42])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:18][CH:17]=2)=[O:41])[CH:27]=[CH:26][C:25]=1[NH:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])=[O:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 6344DichloromethaneHCID 69421103HCID 69421103, compound

Product 1

HCID 10279422HCID 10279422, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent3×

Procedure

A solution of [1-{4-[2-[3-methoxy-4-[3-o-tolyl-ureido]-phenyl]-acetylamino]-phenyl}-cyclopentyl]-acetic acid tert-butyl ester (0.29 g, Reference Example 8) in a mixture of trifluoroacetic acid (7.5 mL), dichloromethane (1.5 mL) and water (1 mL) was stirred at room temperature for 1.5 hours and then evaporated. The residue was chased with toluene to yield a green glass, which was subjected to preparative HPLC [HyperPrep HS C-18 silica column using methanol with 0.05% trifluoroacetic acid and water with 0.05% trifluoroacetic acid as the mobile phase] to give the title compound (0.05 g) as a white solid, m.p. 223–226° C. LC-MS: RT=3.51 minutes, MS(ES+): 538(M+Na+), 516(M+H)+, 554(M+K)+; MS(ES−): 514(M−H)−.

Workup

  1. customevaporated
  2. customto yield a green glass, which

Sources & evidence

ORD record
ord-d292e60bece9461fbfafe6f701aae314
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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