Aluminum(III) Chloride → HCID 86725274, compound

HRID 576650Notes

Reaction equation

HRID 576650 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-c5868f9dbda14c89bd88d1632d47f854
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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