Boron Trichloride → HCID 76903249, compound

HRID 1486151Notes

Reaction equation

C([O:5][C:6](=[O:53])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]([NH:28][C:29](=[O:50])[CH2:30][C:31]2([CH2:46][N+:47]([O-:49])=[O:48])[CH2:36][CH2:35][CH:34]([CH2:37][NH:38]C(OC(C)(C)C)=O)[CH2:33][CH2:32]2)[B:15]2OC3C(C)(C4CC(C3)C4(C)C)[O:16]2)[C:8]=1[O:51]C)(C)(C)C.B(Cl)(Cl)Cl>>[NH2:38][CH2:37][CH:34]1[CH2:35][CH2:36][C:31]([CH2:30][C:29]([NH:28][C@H:14]2[CH2:13][C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([C:6]([OH:5])=[O:53])[C:8]=3[O:51][B:15]2[OH:16])=[O:50])([CH2:46][N+:47]([O-:49])=[O:48])[CH2:32][CH2:33]1

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 86722946HCID 86722946, compound

Product 1

HCID 76903249HCID 76903249, compound

Procedure

Prepared from 3-[2-{2-[4-(tert-Butoxycarbonylamino-methyl)-1-nitromethyl-cyclohexyl]-acetylamino}-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-ethyl]-2-methoxy-benzoic acid tert-butyl ester 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 420 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-434d2c9d96dd49c5a63b0942dafb056c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422314B2

Reaction notes

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