Boron Trichloride → HCID 90271104, compound

HRID 1478863Notes

Reaction equation

C(OC([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:46]=[C:47]([CH2:49][NH:50]C(OC(C)(C)C)=O)[CH:48]=1)[C:13]([NH:15][C@H:16]([B:33]1[O:41]C2C(C)(C3CC(C2)C3(C)C)[O:34]1)[CH2:17][C:18]1[C:19](OC)=[C:20]([CH:28]=[CH:29][CH:30]=1)[C:21]([O:23]C(C)(C)C)=[O:22])=[O:14])=O)(C)(C)C.B(Cl)(Cl)Cl>>[NH2:50][CH2:49][C:47]1[CH:46]=[C:12]([CH:11]=[C:10]([CH2:9][NH2:8])[CH:48]=1)[C:13]([NH:15][C@H:16]1[CH2:17][C:18]2[CH:30]=[CH:29][CH:28]=[C:20]([C:21]([OH:23])=[O:22])[C:19]=2[O:34][B:33]1[OH:41])=[O:14]

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 90271296HCID 90271296, compound

Product 1

HCID 90271104HCID 90271104, compound

Procedure

Prepared from tert-butyl 3-((2R)-2-(3,5-bis((tert-butoxycarbonylamino)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 370 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-5d1d070cdcbf4e21a477b6b9ca544ced
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403850B2

Reaction notes

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