Hydrochloric Acid → HCID 49837191, compound

HRID 2206313Notes

Reaction equation

HRID 2206313 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([NH:15][CH2:16][B:17]([OH:19])[OH:18])(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4].OC(C(O)(C)C)(C)C.Cl>O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][S:12]([NH:15][CH2:16][B:17]([OH:18])[OH:19])(=[O:14])=[O:13])=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735849HCID 131735849, compound

Product 1

HCID 49837191HCID 49837191, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8 (67 mg, 0.18 mmol) and HCl 3 N degassed (3 mL) was allowed to react at reflux for 1 h 30 min. After cooling, the reaction mixture was diluted with water (15 mL) and washed twice with diethyl ether (2×20 mL). The aqueous phase was concentrated in vacuo, affording 9 as a yellow solid (42 mg, 86% yield). Mp 118-122° C. (dec). 1H-NMR (400 MHz, DMSO): δ 2.5 (2H, d, J 4.9, BCH2), 4.42 (2H, s, PhCH2), 6.22 (1H, t, J 4.9, SO2NH), 7.49 (2H, d, J 8.6, H2, H6), 7.93 (2H, d, J 8.6, H3, H5), 7.94 (1H, s, COOH). 13C-NMR (100 MHz, DMSO): δ 31.3 (CB), 55.7, 129.7, 130.7, 131.4, 136.0, 167.6. EI-MS and elemental analysis were not obtainable, but exposure of 9 to an equimolar amount of pinacol in anhydrous THF afforded the corresponding pinacol boronate in quantitative yield and satisfactory elemental analysis; Anal. Calcd. for C15H22BNO6S: C, 50.72; H, 6.24; N, 3.94; S, 9.03. Found: C, 50.88; H, 6.41; N, 3.80; S, 8.77.

Workup

  1. customdegassed (3 mL)
  2. customto react
  3. temperatureat reflux for 1 h 30 min
  4. temperatureAfter cooling
  5. washwashed twice with diethyl ether (2×20 mL)
  6. concentrationThe aqueous phase was concentrated in vacuo

Sources & evidence

ORD record
ord-b88e8c6b841c494b9e6119892c28f02b
Source dataset
uspto-grants-2016_06
Patent number
US09371337B2

Reaction notes

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