Boron Trichloride → (R)-3-(3-((S)-2,3-diaminopropanamido)-4-((dimethylamino)methyl)benzamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid

HRID 2208579Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:49][NH:50]C(OC(C)(C)C)=O)[C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:42]=[CH:43][C:44]=1[CH2:45][N:46]([CH3:48])[CH3:47])[C:9]([NH:11][C@H:12]([B:29]1[O:37]C2C(C)(C3CC(C2)C3(C)C)[O:30]1)[CH2:13][C:14]1[C:15](OC)=[C:16]([CH:24]=[CH:25][CH:26]=1)[C:17]([O:19]C(C)(C)C)=[O:18])=[O:10])=[O:4].B(Cl)(Cl)Cl>>[NH2:1][C@@H:2]([CH2:49][NH2:50])[C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:42]=[CH:43][C:44]=1[CH2:45][N:46]([CH3:48])[CH3:47])[C:9]([NH:11][C@H:12]1[CH2:13][C:14]2[CH:26]=[CH:25][CH:24]=[C:16]([C:17]([OH:19])=[O:18])[C:15]=2[O:37][B:29]1[OH:30])=[O:10])=[O:4]

Participants

Reactant 2

HCID 25135Boron Trichloride

HCID 86725256tert-butyl 3-((2R)-2-(3-((S)-2-amino-3-(tert-butoxycarbonylamino)propanamido)-4-((dimethylamino)methyl)benzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate

Product 1

HCID 76900772(R)-3-(3-((S)-2,3-diaminopropanamido)-4-((dimethylamino)methyl)benzamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid

Procedure

Prepared from tert-butyl 3-((2R)-2-(3-((S)-2-amino-3-(tert-butoxycarbonylamino)propanamido)-4-((dimethylamino)methyl)benzamido)-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 470 (MH)+.

Workup

customThe crude product was purified by reverse phase preparative HPLC
customdried

Sources & evidence

ORD record: ord-7babdca65995494ab10892c1c753fa2e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376454B2

Reaction notes

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