HCID 68281563, compound → HCID 68281487, compound

HRID 1425949Notes

Reaction equation

HRID 1425949 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][C:12](=[O:34])[C@H:13]([NH:26]C(=O)OC(C)(C)C)[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:36])([CH3:35])[O:3]1>Cl.CCOC(C)=O>[NH2:26][C@H:13]([CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=1)[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:36])([CH3:35])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)=[O:34]

Participants

3

Reactant 1

HCID 68281563HCID 68281563, compound

Product 1

HCID 68281487HCID 68281487, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

(R)-tert-butyl 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (1.44 g, 2.844 mmol) was stirred with 4.4 M HCl/EtOAc (10 mL) at room temperature for 30 min. The solution was evaporated to dryness under vacuum to produce (R)-2-amino-N-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-(4-(trifluoromethyl)phenyl)butanamide (CLXIX) as a light orange solid (1.22 g, 2.75 mmol, 97% yield). 1H NMR (DMSO-d6) δ ppm 1.46 (s, 6H), 2.22-2.29 (m, 2H), 2.83-2.91 (m, 2H), 4.17-4.22 (m, 1H), 7.35 (d, 1H, J=8 Hz), 7.47 (d, 2H, J=8 Hz), 7.62 (d, 2H, J=8 Hz), 7.65-7.68 (m, 1H), 7.92 (s, 1H), 8.53 (brs, 3H), 10.76 (s, 1H); 19F NMR (DMSO-d6) δ ppm −60.17 (s, 3F); ESIMS found for C20H22BF3N2O3 m/z 407.4 (M+H), 405.3 (M−H).

Workup

  1. customThe solution was evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-25f4895cd43d4d6493f6d5258b4de4f8
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

Loading…