benzyl (1S,3S,4S)-3-acetamido-3-(tert-butylcarbamoyl)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentylcarbamate → HCID 69669595, compound

HRID 590760Notes

Reaction equation

HRID 590760 reaction equation
[C:1]([NH:4][C@:5]1([C:33](=[O:39])[NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C@@H:9]([CH2:10][CH2:11][CH2:12][B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)[CH2:8][C@H:7]([NH:22]C(=O)OCC2C=CC=CC=2)[CH2:6]1)(=[O:3])[CH3:2]>[OH-].[OH-].[Pd+2].C(OCC)(=O)C.CO>[C:1]([NH:4][C@@:5]1([C:33]([NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:39])[CH2:6][C@@H:7]([NH2:22])[CH2:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][B:13]1[O:17][C:16]([CH3:18])([CH3:19])[C:15]([CH3:20])([CH3:21])[O:14]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86665798benzyl (1S,3S,4S)-3-acetamido-3-(tert-butylcarbamoyl)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentylcarbamate

Product 1

HCID 69669595HCID 69669595, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

While under nitrogen, a stirred solution of benzyl (1S,3S,4S)-3-acetamido-3-(tert-butylcarbamoyl)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentylcarbamate (0.544 g, 1.00 mmol) in 4:1 ethyl acetate/methanol (20 mL) was treated with 20% Pd(OH)2/C (0.30 g), purged with hydrogen, and stirred under a balloon for 18 h. The mixture was purged with nitrogen and carefully filtered through a pad of Celite® (without letting filter pad dry) and the filtrate concentrated in vacuo to afford 0.409 g (100%) of the subject compound as a white solid. NMR (CDCl3): δ 6.72 (br s, 1 H), 6.67 (br s, 1 H), 3.63 (m, 1 H), 2.80 (m, 1 H), 2.57 (m, 1 H), 1.75-2.00 (m, 4 H), 1.93 (s, 3 H), 1.00-1.50 (m, 3 H), 1.25 (s, 9 H), 1.17 (s, 12 H), 0.60-0.75 (m, 2 H). MS (M+1): 410.5.

Workup

  1. custompurged with hydrogen
  2. customThe mixture was purged with nitrogen
  3. filtrationcarefully filtered through a pad of Celite® (without letting filter pad dry)
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-891f00ed5c8a4959aedbc21e8a45f6eb
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Reaction notes

Loading…