Dichloromethane → HCID 69536247, compound

HRID 1017984Notes

Reaction equation

HRID 1017984 reaction equation
C([O:5][C:6](=[O:44])[CH2:7][CH:8]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:43])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:32])=[C:26]([O:41][CH3:42])[CH:25]=2)=[CH:17][CH:16]=1)[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)(C)(C)C.FC(F)(F)C(O)=O.[Cl:52]CCl>>[ClH:52].[CH3:42][O:41][C:26]1[CH:25]=[C:24]([CH2:23][C:22]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([CH:8]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[CH2:7][C:6]([OH:44])=[O:5])=[CH:16][CH:17]=2)=[O:43])[CH:29]=[CH:28][C:27]=1[NH:30][C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:40])=[O:32]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 54304223HCID 54304223, compound

Product 1

HCID 69536247HCID 69536247, compound

Procedure

A mixture of 3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}phenyl)-3-(morpholin-4-yl)-propanoic acid tert-butyl ester [100 mg, Reference Example 11(a)] anhydrous trifluoroacetic acid (3 ml) and dichloromethane (5 ml) allowed to stand at ambient temperature for 1 hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 1.0M hydrochloric acid. The aqueous layer was evaporated and the residue was triturated with a mixture of methanol and diethyl ether to yield the title compound (46 mg) as a white solid, m.p. 164-171° C. (amorphous). MS: MH+ 547.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1.0M hydrochloric acid
  3. customThe aqueous layer was evaporated
  4. customthe residue was triturated with a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-caf2a7da3924457e91e399eb7298b4d9
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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