2-(((Tert-butoxy)carbonyl)amino)-4,4,4-trifluorobutanoic acid → 1-(S)-[N'-(2-Amino-4,4,4-trifluorobutyryl)-L-alaninyl]-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one

HRID 413874Notes

Reaction equation

HRID 413874 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([C@@H:7]1[C:13]2[CH:14]=[CH:15][CH2:16][CH2:17][C:12]=2[CH2:11][CH:10]([NH2:18])[N:9]([CH3:19])[C:8]1=[O:20])=[O:6])[CH3:4].C([NH:28][CH:29]([CH2:33][C:34]([F:37])([F:36])[F:35])[C:30](O)=[O:31])(OC(C)(C)C)=O>>[NH2:28][CH:29]([CH2:33][C:34]([F:37])([F:36])[F:35])[C:30]([NH:2][C@H:3]([C:5]([C@@H:7]1[C:13]2[CH:14]=[CH:15][CH2:16][CH2:17][C:12]=2[CH2:11][CH:10]([NH2:18])[N:9]([CH3:19])[C:8]1=[O:20])=[O:6])[CH3:4])=[O:31]

Participants

3

Reactant 2

HCID 120980572-(((Tert-butoxy)carbonyl)amino)-4,4,4-trifluorobutanoic acidHCID 697365561-(S)-[L-alaninyl]-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one hydrochloride

Product 1

HCID 865926041-(S)-[N'-(2-Amino-4,4,4-trifluorobutyryl)-L-alaninyl]-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one

Procedure

Following General Procedure D above using 1-(S)-[L-alaninyl]-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one hydrochloride (Example 7-30, below) and 2-(N-Boc-amino)-4,4,4-trifluorobutyric acid (Oakwood), the protected intermediate was prepared. The Boc-group was removed using 5.0 M HCl in dioxane and the resulting free-base purified by flash chromatography CHCl3/MeOH (97.3) yielding the title compounds.

Workup

  1. customthe protected intermediate was prepared
  2. customThe Boc-group was removed
  3. customthe resulting free-base purified by flash chromatography CHCl3/MeOH (97.3)

Sources & evidence

ORD record
ord-ba16f51cc99141d38a77a4f6179cac8f
Source dataset
uspto-grants-2003_05
Patent number
US06569851B1

Reaction notes

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