Aluminum(III) Chloride → HCID 86725274, compound

HRID 2208611Notes

Reaction equation

HRID 2208611 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C([O:9][C:10](=[O:42])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH:18]([NH:32][C:33]([C:35]2[O:39][CH:38]=[N:37][CH:36]=2)=[O:34])[B:19]2[O:27]C3C(C)(C4CC(C3)C4(C)C)[O:20]2)[C:12]=1OC)(C)(C)C>C(Cl)Cl>[OH:20][B:19]1[C@@H:18]([NH:32][C:33]([C:35]2[O:39][CH:38]=[N:37][CH:36]=2)=[O:34])[CH2:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([OH:9])=[O:42])[C:12]=2[O:27]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86725275HCID 86725275, compound

Product 1

HCID 86725274HCID 86725274, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (0.132 g, 0.990 mmol) was added to a solution of 2-Methoxy-3-[2-[(oxazole-5-carbonyl)-amino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-ethyl]-benzoic acid tert-butyl ester (0.064 g, 0.122 mmol) in CH2Cl2 (3.0 mL). The reaction was stirred at room temperature for 16 hr. The reaction was quenched with H2O and CH3OH and extracted with hexane (2×). The crude product remained in the aqueous layer and was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 303 (MH)+.

Workup

  1. customThe reaction was quenched with H2O and CH3OH
  2. extractionextracted with hexane (2×)
  3. customwas purified by reverse phase preparative HPLC
  4. customdried

Sources & evidence

ORD record
ord-7d483867fbaf495d948d716ad911360b
Source dataset
uspto-grants-2016_06
Patent number
US09376454B2

Reaction notes

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