Boron Trichloride → HCID 76900771, compound

HRID 1478841Notes

Reaction equation

C(OC([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([CH:47]=[CH:48][C:49]=1[CH2:50][N:51]([C:53](OC(C)(C)C)=O)C)[C:14]([NH:16][C@H:17]([B:34]1[O:42]C2C(C)(C3CC(C2)C3(C)C)[O:35]1)[CH2:18][C:19]1[C:20](OC)=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24]C(C)(C)C)=[O:23])=[O:15])[CH3:9])=O)(C)(C)C.B(Cl)(Cl)Cl>>[CH3:9][NH:8][CH2:10][C:11]1[CH:12]=[C:13]([CH:47]=[CH:48][C:49]=1[CH2:50][NH:51][CH3:53])[C:14]([NH:16][C@H:17]1[CH2:18][C:19]2[CH:31]=[CH:30][CH:29]=[C:21]([C:22]([OH:24])=[O:23])[C:20]=2[O:42][B:34]1[OH:35])=[O:15]

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 90271339HCID 90271339, compound

Product 1

HCID 76900771HCID 76900771, compound

Procedure

Prepared from tert-butyl 3-((2R)-2-(3,4-bis((tert-butoxycarbonyl(methyl)amino)methyl)benzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate 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 398 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-c0a9e1453f3e47d58d80cd63912c182c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403850B2

Reaction notes

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