HCID 10399143, compound → HCID 86741422, compound

HRID 542646Notes

Reaction equation

HRID 542646 reaction equation
O.[CH3:2][N:3]([CH3:17])[CH2:4][C@H:5]([C:14]([OH:16])=O)[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH3:18][CH:19]([CH3:34])[CH2:20][CH2:21][NH:22][C:23](=[O:33])[C@H:24]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH2:25]>O1CCCC1>[CH3:17][N:3]([CH3:2])[CH2:4][C@H:5]([C:14]([NH:25][C@H:24]([C:23]([NH:22][CH2:21][CH2:20][CH:19]([CH3:34])[CH3:18])=[O:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:16])[NH:6][C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]

Participants

4

Reactant 2

HCID 10399143HCID 10399143, compoundHCID 86741423HCID 86741423, compound

Product 1

HCID 86741422HCID 86741422, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the method of part A of Example 1, in two runs, and using tetrahydrofuran instead of acetone as solvent 3-dimethylamino-N2 -(t-butoxycarbonyl)-D-alanine monohydrate (1.00 g., 716 mg.) was condensed with N-(3-methylbutyl)-L-phenylalaninamide (part D of Example 1, 1.05 g., 760 mg.). The products (2.06 g., 1.21 g.) were combined and purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel using ammonium acetate (0.2%) in methanol-water (70:30) as the eluant, affording [3-dimethylamino-N2 -(t-butoxycarbonyl)-D-alanyl]-N-(3-methylbutyl)-L-phenylalaninamide as an oil (1.96 g.).

Workup

  1. custompurified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel

Sources & evidence

ORD record
ord-a80ec9ebf6d946b48118056b026f923f
Source dataset
uspto-grants-1987_04
Patent number
US04658013

Reaction notes

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