Hydrochloric Acid → HCID 178520747, compound

HRID 1404347Notes

Reaction equation

HRID 1404347 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][C:19]([NH:21][C@H:22]2[CH2:27][C:26]3[CH:28]=[CH:29][CH:30]=[C:31]([C:32]([OH:34])=[O:33])[C:25]=3[O:24][B:23]2[OH:35])=[O:20])[CH2:14][CH2:13]1)(C(C)(C)C)(C)C.Cl>O1CCOCC1>[OH:35][B:23]1[C@@H:22]([NH:21][C:19](=[O:20])[CH2:18][C@H:15]2[CH2:16][CH2:17][C@H:12]([NH:11][CH2:10][CH2:9][OH:8])[CH2:13][CH2:14]2)[CH2:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:31]([C:32]([OH:34])=[O:33])[C:25]=2[O:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178455266HCID 178455266, compound

Product 1

HCID 178520747HCID 178520747, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To (R)-3-(2-(trans-4-(2-(tert-butyldimethylsilyloxy)ethylamino)cyclohexyl)acetamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid from step 1 (100 mg) in a flask was added 4 mL 4N HCl in dioxane. The resulting reaction mixture was stirred at RT for 2 hr. The solvent was removed in vacuo and the residue was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 391 (MH)+.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by reverse phase preparative HPLC
  4. customdried

Sources & evidence

ORD record
ord-163938079ea94b4f848cab1e4c7d8d2d
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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