Boron Trichloride → HCID 178483957, compound

HRID 1486138Notes

Reaction equation

[CH3:1][N:2]([CH3:44])[CH2:3][C:4]([NH:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][C:15]([NH:17][C@H:18]([B:31]2[O:39]C3C(C)(C4CC(C3)C4(C)C)[O:32]2)[CH2:19][C:20]2[C:21](OC)=[C:22]([CH:26]=[CH:27][CH:28]=2)[C:23]([OH:25])=[O:24])=[O:16])[CH2:10][CH2:9]1)=[O:5].B(Cl)(Cl)Cl>>[CH3:1][N:2]([CH3:44])[CH2:3][C:4]([NH:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][C:15]([NH:17][C@H:18]2[CH2:19][C:20]3[CH:28]=[CH:27][CH:26]=[C:22]([C:23]([OH:25])=[O:24])[C:21]=3[O:32][B:31]2[OH:39])=[O:16])[CH2:10][CH2:9]1)=[O:5]

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 178491868HCID 178491868, compound

Product 1

HCID 178483957HCID 178483957, compound

Procedure

Prepared from 3-((2R)-2-(2-(trans-4-((2-(dimethylamino)acetamido)methyl)cyclohexyl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoic acid and BCl3 following the procedure described in Step 2 of Example 1. The crude product was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 446 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-2c28a0f74f894d6ea2f8e76d12de886a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422314B2

Reaction notes

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