Silane, tris(1-methylethyl)- → HCID 178525577, compound

HRID 1860335Notes

Reaction equation

HRID 1860335 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([NH:15][C@H:16]([C:25]([NH:27][CH2:28][CH2:29][C:30]2[CH:37]=[CH:36][C:34]([OH:35])=[C:32]([OH:33])[CH:31]=2)=[O:26])[CH2:17][C:18](=[O:24])[O:19]C(C)(C)C)=[O:14])[CH:3]=1.C([SiH](C(C)C)C(C)C)(C)C>>[OH:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([NH:15][C@H:16]([C:25]([NH:27][CH2:28][CH2:29][C:30]2[CH:37]=[CH:36][C:34]([OH:35])=[C:32]([OH:33])[CH:31]=2)=[O:26])[CH2:17][C:18](=[O:19])[OH:24])=[O:14])[CH:3]=1

Participants

3

Reactant 2

HCID 138754Silane, tris(1-methylethyl)-HCID 178451087HCID 178451087, compound

Product 1

HCID 178525577HCID 178525577, compoundYield 57%

Procedure

The title compound was prepared by hydrolysis of the tert-butyl protective group of N-[Nα-(4,8-dihydroxyquinoline-2-carbonyl)-Oγ-tert-butyl-L-aspartyl]dopamine prepared in example 62, step B (121 mg, 2.4 mmol) using the indications of general procedure C in the presence of triisopropylsilane (187 mg, 1.2 mmol). Purification by flash chromatography using 50% EtOAc/CH2Cl2/1% AcOH yielded the desired product as a yellow powder (61 mg, 57%).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-ad8df350932f4565ace6e48110f8d558
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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