Hydrochloric Acid → HCID 76901335, compound

HRID 1478870Notes

Reaction equation

HRID 1478870 reaction equation
CO[C:3]1[C:11]([CH2:12][CH:13]([NH:27][C:28](=[O:40])[CH2:29][C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[CH2:35][N:34]([CH3:39])[CH2:33]3)[B:14]2[O:22]C3C(C)(C4CC(C3)C4(C)C)[O:15]2)=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].Cl>O1CCOCC1>[OH:15][B:14]1[C@@H:13]([NH:27][C:28](=[O:40])[CH2:29][C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[CH2:35][N:34]([CH3:39])[CH2:33]3)[CH2:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=2[O:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86725267HCID 86725267, compound

Product 1

HCID 76901335HCID 76901335, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-Methoxy-3-[2-[2-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)-acetylamino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-ethyl]-benzoic acid (0.113 g, 0.207 mmol) and 1,4-dioxane (2.0 mL) was added 3N HCl (1.7 mL, 5.10 mmol) and the reaction was heated at 100° C. for 1 hr. The reaction was cooled to room temperature and extracted with diethyl ether (3×). The product remained in the aqueous layer and was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 381 (MH)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with diethyl ether (3×)
  3. customwas purified by reverse phase preparative HPLC
  4. customdried

Sources & evidence

ORD record
ord-2ce6afceaddf40fda613e7174f02d55e
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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