Boron Trichloride → HCID 76900586, compound

HRID 1478833Notes

Reaction equation

CO[C:3]1[C:15]([CH2:16][C@H:17]([NH:31][C:32]([C:34]2[CH:35]=[C:36]3[C:40](=[CH:41][CH:42]=2)[CH2:39][N:38]([CH2:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)[CH2:37]3)=[O:33])[B:18]2[O:26]C3C(C)(C4CC(C3)C4(C)C)[O:19]2)=[CH:14][CH:13]=[CH:12][C:4]=1[C:5]([O:7]C(C)(C)C)=[O:6].B(Cl)(Cl)Cl>>[OH:26][B:18]1[C@@H:17]([NH:31][C:32]([C:34]2[CH:35]=[C:36]3[C:40](=[CH:41][CH:42]=2)[CH2:39][N:38]([CH2:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)[CH2:37]3)=[O:33])[CH2:16][C:15]2[CH:14]=[CH:13][CH:12]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=2[O:19]1

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 86725242HCID 86725242, compound

Product 1

HCID 76900586HCID 76900586, compound

Procedure

Prepared from tert-butyl 2-methoxy-3-((2R)-2-(2-(pyridin-3-ylmethyl)isoindoline-5-carboxamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)benzoate and BCl3 following the procedure described in Step 2 of Example 3. The crude product was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 344 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-9604000fa5a34f63aaff3cf2dba263b7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403850B2

Reaction notes

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