Boron Trichloride → HCID 178484310, compound

HRID 1404387Notes

Reaction equation

C(OC([N:8]([CH2:51][CH2:52][N:53]([C:55](OC(C)(C)C)=O)C)[C@H:9]1[CH2:14][CH2:13][C@H:12]([CH:15]([CH2:49][OH:50])[C:16]([NH:18][C@H:19]([B:36]2[O:44]C3C(C)(C4CC(C3)C4(C)C)[O:37]2)[CH2:20][C:21]2[C:22](OC)=[C:23]([CH:31]=[CH:32][CH:33]=2)[C:24]([O:26]C(C)(C)C)=[O:25])=[O:17])[CH2:11][CH2:10]1)=O)(C)(C)C.B(Cl)(Cl)Cl>>[OH:37][B:36]1[C@@H:19]([NH:18][C:16](=[O:17])[CH:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([NH:8][CH2:51][CH2:52][NH:53][CH3:55])[CH2:10][CH2:11]2)[CH2:49][OH:50])[CH2:20][C:21]2[CH:33]=[CH:32][CH:31]=[C:23]([C:24]([OH:26])=[O:25])[C:22]=2[O:44]1

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 178491878HCID 178491878, compound

Product 1

HCID 178484310HCID 178484310, compound

Procedure

Prepared from tert-butyl 3-((2R)-2-(2-(trans-4-(tert-butoxycarbonyl(2-(tert-butoxycarbonyl(methyl)amino)ethyl)amino)cyclohexyl)-3-hydroxypropanamido)-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 1. The crude product was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 434 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-32a72a5eb0c045bc85b724847e849de7
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912169B2

Reaction notes

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