Boron Trichloride → HCID 76900585, compound

HRID 1478831Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]([NH:22][C@H:23]([B:40]3[O:48]C4C(C)(C5CC(C4)C5(C)C)[O:41]3)[CH2:24][C:25]3[C:26](OC)=[C:27]([CH:35]=[CH:36][CH:37]=3)[C:28]([O:30]C(C)(C)C)=[O:29])=[O:21])[CH:17]=2)[CH2:12]1)=O)(C)(C)C.B(Cl)(Cl)Cl>>[NH2:8][CH2:9][CH2:10][N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]([NH:22][C@H:23]3[CH2:24][C:25]4[CH:37]=[CH:36][CH:35]=[C:27]([C:28]([OH:30])=[O:29])[C:26]=4[O:48][B:40]3[OH:41])=[O:21])[CH:17]=2)[CH2:12]1

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 86725240HCID 86725240, compound

Product 1

HCID 76900585HCID 76900585, compound

Procedure

Prepared from tert-butyl 3-((2R)-2-(2-(2-(tert-butoxycarbonylamino)ethyl)isoindoline-5-carboxamido)-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 396 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-fcf2cb4232064725ba83ece17468427a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403850B2

Reaction notes

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