Trifluoroacetic acid → HCID 22960334, compound

HRID 2304373Notes

Reaction equation

HRID 2304373 reaction equation
C([O:5][C:6](=[O:33])[C@H:7]([CH3:32])[NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH2:27][CH2:28][Cl:29])[CH2:24][CH2:25][Cl:26])=[C:19]([CH3:30])[CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28][Cl:29])[C:20]1[CH:21]=[CH:22][C:17]([O:16][C:13]2[CH:12]=[CH:11][C:10]([C:9]([NH:8][C@H:7]([C:6]([OH:33])=[O:5])[CH3:32])=[O:31])=[CH:15][CH:14]=2)=[CH:18][C:19]=1[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22960337HCID 22960337, compound2×

Product 1

HCID 22960334HCID 22960334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-{4-[bis-(2-chloroethyl)-amino]-3-methyl-phenoxy}-benzoyl)-L-alanine-tert-butyl ester (400 mg; compound 9) was dissolved in dichloromethane (4 ml) and trifluoroacetic acid (8 ml) was added. The mixture was allowed to stand at ambient temperature for 1 hour, evaporated to dryness and azeotroped twice with ethyl acetate to give the titled compound (compound 10; the drug corresponding with the prodrug of Example 21) as an oil (0.43 g, 52% yield).

Workup

  1. customevaporated to dryness
  2. customazeotroped twice with ethyl acetate

Sources & evidence

ORD record
ord-4218e8df5c6a4537ba0f156e44b77ae6
Source dataset
uspto-grants-2002_08
Patent number
US06436691B1

Reaction notes

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