HCID 22942158, compound → 5-[2-[1 (RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvaleric acid

HRID 850888Notes

Reaction equation

HRID 850888 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([NH:26][CH:27]([B:30]3[O:34][C:33]([CH2:36][CH2:37][CH:38]([CH3:47])[CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])([CH3:35])[C:32]([CH3:49])([CH3:48])[O:31]3)[CH2:28][CH3:29])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O.ClCCl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([NH:26][CH:27]([B:30]3[O:34][C:33]([CH2:36][CH2:37][CH:38]([CH3:47])[CH2:39][C:40]([OH:42])=[O:41])([CH3:35])[C:32]([CH3:48])([CH3:49])[O:31]3)[CH2:28][CH3:29])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 22942158HCID 22942158, compound

Product 1

HCID 229420655-[2-[1 (RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvaleric acidYield 100.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

50 mg (0.074 mmol) of tert-butyl 5-[2-[1(RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4(RS) ,5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvalerate were dissolved in 1 ml of trifluoroacetic acid and 1 ml of dichloromethane. The solution was stirred at room temperature for 15 minutes and then evaporated under a vacuum. The residue was co-evaporated with toluene to give 46 mg of 5-[2-[1 (RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvaleric acid as an oil; MS: m/e 621 [M+H]+.

Workup

  1. customevaporated under a vacuum

Sources & evidence

ORD record
ord-49db4f493ed64665af95ad81aa073f45
Source dataset
uspto-grants-2000_01
Patent number
US06018020

Reaction notes

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