Hydrogen chloride-ethyl acetate → HCID 68281476, compound

HRID 1425945Notes

Reaction equation

HRID 1425945 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][C:12](=[O:33])[C@H:13]([NH:25]C(=O)OC(C)(C)C)[CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:35])([CH3:34])[O:3]1.Cl.CCOC(C)=O>>[NH2:25][C@H:13]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=1)[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:35])([CH3:34])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)=[O:33]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86702805HCID 86702805, compound

Product 1

HCID 68281476HCID 68281476, compoundYield 95.7%

Procedure

(R)-tert-butyl 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (CLXII) (1.00 g, 2.1 mmol) was treated with HCl/EtOAc (4.2 M, 15 mL) and was stirred for 30 minutes at room temperature. The solvent was removed under vacuum, and the residue was triturated with hexane to give the hydrochloride salt of (R)-2-amino-N-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-3-(4-(trifluoromethyl)phenyl)propanamide (CLXIII) as a white solid (0.86 g, 2.01 mmol, 94% yield). 1H NMR (DMSO-d6) δ ppm 1.39 (s, 6H), 3.19 (dd, J=13 Hz, J=13 Hz, 1H), 3.29-3.32 (m, 1H), 4.33-4.40 (m, 1H), 7.34 (d, J=8 Hz, 1H), 7.55 (d, J=7 Hz, 2H), 7.60 (d, J=8 Hz, 1H), 7.66 (d, J=7 Hz, 2H), 7.86 (s, 1H), 8.45 (brs, 3H), 9.1 (s, 1H), 11.03 (s, 1H); 19F NMR (DMSO-d6) δ ppm −60.25 (s, 3F). ESIMS found for C19H20BF3N2O3 m/z 393.4 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-fd5c4881dd67439093daed3d091d1e2d
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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