HCID 506297, compound → HCID 508023, compound

HRID 1368168Notes

Reaction equation

HRID 1368168 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:31])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([C:27]([O:29]C)=[O:28])[CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:17])[C@H:11]([CH3:32])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:31])[C:16]([CH:18]2[C:26]3[C:21](=[C:22]([C:27]([OH:29])=[O:28])[CH:23]=[CH:24][CH:25]=3)[NH:20][CH2:19]2)=[O:17])[C@H:11]([CH3:32])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 506297HCID 506297, compound

Product 1

HCID 508023HCID 508023, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

1-(benzoyl)-3-(R)-methyl4-[(7-(methoxycarbonyl)indol-3-yl)-2-oxoacetyl]piperazine (50 mg) was dissolved in a solution of triethylsilane (Et3SiH, 0.5 mL) in TFA (5 mL). The reaction was stirred for 10 hours. Solvents were removed under vaccum, and the residue was purified using Shimadzu automated preparative HPLC System to give 1-benzoyl-3-(R)-methyl-4-[(7-carboxyindolin-3-yl)-2-oxoacetyl]piperazine (5.5 mg).

Workup

  1. customSolvents were removed under vaccum
  2. customthe residue was purified

Sources & evidence

ORD record
ord-1866c7f0c67d4116b620a74824179411
Source dataset
uspto-grants-2003_06
Patent number
US06573262B2

Reaction notes

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