Boron Trichloride → HCID 178511527, compound

HRID 1404327Notes

Reaction equation

C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]([NH:18][C@H:19]([B:32]2OC3C(C)(C4CC(C3)C4(C)C)[O:33]2)[CH2:20][C:21]2[C:22]([O:30]C)=[C:23]([CH:27]=[CH:28][CH:29]=2)[C:24]([OH:26])=[O:25])=[O:17])[CH2:11][CH2:10]1)=O)(C)(C)C.B(Cl)(Cl)Cl>>[NH2:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][C:16]([NH:18][C@H:19]2[CH2:20][C:21]3[CH:29]=[CH:28][CH:27]=[C:23]([C:24]([OH:26])=[O:25])[C:22]=3[O:30][B:32]2[OH:33])=[O:17])[CH2:13][CH2:14]1

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 178491875HCID 178491875, compound

Product 1

HCID 178511527HCID 178511527, compound

Procedure

Prepared from 3-((2R)-2-(2-(cis-4-(tert-butoxycarbonylamino)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 347 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-74a2a266de584c28bb946f593a0362be
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912169B2

Reaction notes

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