Boron Trichloride → HCID 90271185, compound

HRID 1478883Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:52]=[CH:51][CH:50]=[CH:49][C:15]=1[C:16]([NH:18][C@H:19]([B:36]1[O:44]C2C(C)(C3CC(C2)C3(C)C)[O:37]1)[CH2:20][C:21]1[C:22](OC)=[C:23]([CH:31]=[CH:32][CH:33]=1)[C:24]([O:26]C(C)(C)C)=[O:25])=[O:17])=[O:13])=O)(C)(C)C.B(Cl)(Cl)Cl>>[NH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:52]=[CH:51][CH:50]=[CH:49][C:15]=1[C:16]([NH:18][C@H:19]1[CH2:20][C:21]2[CH:33]=[CH:32][CH:31]=[C:23]([C:24]([OH:26])=[O:25])[C:22]=2[O:44][B:36]1[OH:37])=[O:17])=[O:13]

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 86725278HCID 86725278, compound

Product 1

HCID 90271185HCID 90271185, compound

Procedure

Prepared from tert-butyl 3-((2R)-2-(2-(2-(tert-butoxycarbonylamino)ethylcarbamoyl)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 product was then purified by reverse phase HPLC and dried using lyophilization. ESI-MS m/z 398 (MH)+.

Workup

customThe product was then purified by reverse phase HPLC
customdried

Sources & evidence

ORD record: ord-8d9bfb82a2f547728368d1eae8b438f2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403850B2

Reaction notes

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