Water → HCID 9848138, compound

HRID 1375065Notes

Reaction equation

HRID 1375065 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:39])[CH2:21][C:22]3[CH:38]=[CH:37][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.ClCCl.O>FC(F)(F)C(O)=O>[C:31]1([CH3:36])[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:27]1[O:28][C:24]2[CH:23]=[C:22]([CH2:21][C:20]([NH:19][C:16]3[CH:15]=[CH:14][C:13]([C:8]4([CH2:7][C:6]([OH:40])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9]4)=[CH:18][CH:17]=3)=[O:39])[CH:38]=[CH:37][C:25]=2[N:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 69418113HCID 69418113, compound

Product 1

HCID 9848138HCID 9848138, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [1-{4-[2-[2-o-tolylamino-benzoxazol-6-yl]-acetylamino]-phenyl}-cyclopentyl]-acetic acid tert-butyl ester [0.36 g, Reference Example 1(a)] in a mixture of trifluoroacetic acid (12 mL), dichloromethane (2.25 mL) and water (1.5 mL) was stirred at room temperature for 1.5 hours. The resulting turquoise solution was evaporated and the residue was chased with toluene to yield an amber gum which was recrystallised from a mixture of acetonitrile and water to give the title compound (0.25 g) as an off white solid, m.p. 123–126° C. LC-MS: RT=3.51 minutes, MS(ES+): 506.6(M+Na)+, 484.6(M+H)+; MS(ES−): 482.4(M−H)−.

Workup

  1. customThe resulting turquoise solution was evaporated
  2. customto yield an amber gum which
  3. customwas recrystallised from a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-921fb72f881a4fa795cb178225f7216c
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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