(2S)-2-(((tert-butoxy)carbonyl)amino)-4,4,4-trifluoro-3-(trifluoromethyl)butanoic acid → 1-(S)-[N'-(Hexafluorovalinyl)-L-alaninyl]-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one

HRID 413875Notes

Reaction equation

HRID 413875 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][C@H:29]([C:39](O)=[O:40])[CH:30]([C:35]([F:38])([F:37])[F:36])[C:31]([F:34])([F:33])[F:32])(OC(C)(C)C)=O>>[F:32][C:31]([F:33])([F:34])[CH:30]([C:35]([F:36])([F:38])[F:37])[C@@H:29]([C:39]([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:40])[NH2:28]

Participants

3

Reactant 2

HCID 26599218(2S)-2-(((tert-butoxy)carbonyl)amino)-4,4,4-trifluoro-3-(trifluoromethyl)butanoic acidHCID 697365561-(S)-[L-alaninyl]-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one hydrochloride

Product 1

HCID 1317239011-(S)-[N'-(Hexafluorovalinyl)-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 N-Boc-hexafluorovaline (Aldrich), the protected intermediate was prepared. The Boc-group was removed using 5.0 M HCl in dioxane and the resulting free-base purified by chromatography CHCl3/MeOH (95:5) yielding the title compound as a mixture of diastereomers.

Workup

  1. customthe protected intermediate was prepared
  2. customThe Boc-group was removed
  3. customthe resulting free-base purified by chromatography CHCl3/MeOH (95:5)

Sources & evidence

ORD record
ord-4729e381564d4120840324246062c76b
Source dataset
uspto-grants-2003_05
Patent number
US06569851B1

Reaction notes

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