Hydrochloric Acid → HCID 57969140, compound

HRID 1471614Notes

Reaction equation

HRID 1471614 reaction equation
C(OC(=O)[NH:7][CH:8]([C:16](=[O:36])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:35]=[CH:34][C:29]3[B:30]([OH:33])[O:31][CH2:32][C:28]=3[CH:27]=2)=[CH:21][CH:20]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.Cl>C(Cl)Cl>[NH2:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]([NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:35]=[CH:34][C:29]3[B:30]([OH:33])[O:31][CH2:32][C:28]=3[CH:27]=2)=[CH:23][CH:24]=1)=[O:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57969056HCID 57969056, compound

Product 1

HCID 57969140HCID 57969140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 mL scintillation vial {1-[4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-benzylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (190 mg, 0.38 mmol, 1.0 eq.) in DCM (5.0 mL) was added HCl (5.0 mL, 4.0M in 1,4-dioxane) and the mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure to give 2-amino-N-[4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-benzyl]-3-phenyl-propionamid as a light yellow glassy solid. LCMS (m/z) 403 (M+H); 1H NMR (DMSO-d6) δ: 8.91 (br. s., 1H), 8.32 (br. s., 3H), 7.70 (d, J=8.0 Hz, 1H), 7.23-7.33 (m, 4H), 7.19-7.23 (m, 2H), 7.11 (d, J=8.6 Hz, 2H), 6.88-6.99 (m, 4H), 4.90 (s, 2H), 4.27-4.35 (m, 1H), 4.15-4.24 (m, 1H), 3.98-4.06 (m, 1H), 3.04 (d, J=7.2 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e3833caa4204799ba35e1291a8ce839
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

Loading…