(S)-benzyl 4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoate → (S)-4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoic acid

HRID 1425951Notes

Reaction equation

HRID 1425951 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([NH:24][C@H:25]([CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=1)[C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]2[C:36]([CH3:38])([CH3:37])[O:35][B:34]([OH:39])[C:33]=2[CH:40]=1)=[O:27])=[O:23])[CH2:10][CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.O.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([NH:24][C@H:25]([CH2:41][CH2:42][C:43]1[CH:44]=[CH:45][C:46]([C:49]([F:51])([F:52])[F:50])=[CH:47][CH:48]=1)[C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]2[C:36]([CH3:37])([CH3:38])[O:35][B:34]([OH:39])[C:33]=2[CH:40]=1)=[O:27])=[O:23])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86702808(S)-benzyl 4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoate

Product 1

HCID 68281384(S)-4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of (S)-benzyl 4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoate (1.8 g, 2.48 mmol) in a mixture of EtOH/H2O (20 mL/2 mL) was added Pd(OH)2/C (cat.). The mixture was stirred under a H2 atmosphere for 2 h. The mixture was filtered through Celite and washed with MeOH. The filtrate was evaporated to dryness under vacuum to produce (S)-4-(tert-butoxycarbonylamino)-5-((R)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylamino)-5-oxopentanoic acid (CLXXI) as a white foam (1.57 g, 2.48 mmol, 100% yield). ESIMS found for C30H37BF3N3O3 m/z 634.6 (M−H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with MeOH
  3. customThe filtrate was evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-3def36f5209d4527bf65ca2cf6da3e1f
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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