HCID 86619925, compound → HCID 59718699, compound

HRID 2219030Notes

Reaction equation

HRID 2219030 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[C@@H:16]([NH:19][C:20](=[O:35])[C:21]([OH:34])([CH3:33])[C:22]([NH:24][CH2:25][C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[O:23])[CH2:15][N:14]([CH2:36][C:37]([F:40])([F:39])[F:38])[C:13]2[CH:41]=[CH:42][CH:43]=[CH:44][C:12]1=2)C1C=CC=CC=1>[Pd]>[OH:34][C:21]([CH3:33])([C:22]([NH:24][CH2:25][C:26]([F:32])([F:31])[C:27]([F:28])([F:29])[F:30])=[O:23])[C:20]([NH:19][C@@H:16]1[C:17](=[O:18])[N:11]([CH2:10][CH2:9][OH:8])[C:12]2[CH:44]=[CH:43][CH:42]=[CH:41][C:13]=2[N:14]([CH2:36][C:37]([F:39])([F:40])[F:38])[CH2:15]1)=[O:35]

Participants

3

Reactant 1

HCID 86619925HCID 86619925, compound

Product 1

HCID 59718699HCID 59718699, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In an analogous procedure to that described in Example 8d), the hydrogenolysis of the first eluting epimer (R or S)-(−)-N-[(S)-1-(2-benzyloxy-ethyl)-2-oxo-5-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-2-hydroxy-2-methyl-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide using palladium on carbon (10%) as the catalyst yielded the title compound as a white foam (yield 75% of theory); MS (m/e): 551 (M+H)+.

Sources & evidence

ORD record
ord-d125321382bc4739a5819ff5f71aa438
Source dataset
uspto-grants-2008_08
Patent number
US07414049B2

Reaction notes

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