Hydrochloric Acid → HCID 68526470, compound

HRID 1182693Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:3]([NH:5][C@@H:6]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]([NH:9][C@H:10]([B:16]1[O:20][C@@H:19]2[CH2:21][C@@H:22]3[CH2:25][C@H:24]([C@:18]2([CH3:28])[O:17]1)[C:23]3([CH3:27])[CH3:26])[CH2:11][CH:12]1[CH2:15][CH2:14][CH2:13]1)=[O:8])=[O:4].Cl.C(#N)C.[C:48](OC(=O)C)(=[O:50])[CH3:49].C(N(CC)C(C)C)(C)C>>[C:48]([NH:1][C@@H:2]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:3]([NH:5][C@@H:6]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]([NH:9][C@H:10]([B:16]1[O:20][C@@H:19]2[CH2:21][C@@H:22]3[CH2:25][C@H:24]([C@:18]2([CH3:28])[O:17]1)[C:23]3([CH3:26])[CH3:27])[CH2:11][CH:12]1[CH2:15][CH2:14][CH2:13]1)=[O:8])=[O:4])(=[O:50])[CH3:49]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 6342Acetonitrile

HCID 7918Acetic Anhydride

HCID 81531Diisopropylethylamine

HCID 68527816HCID 68527816, compound

Product 1

HCID 68526470HCID 68526470, compoundYield 53%

Procedure

Into a 20 mL scintillation vial was added (2S)-2-amino-N-[(1S)-1-benzyl-2-({(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}amino)-2-oxoethyl]-4-phenylbutanamide.HCl (52.0 mg, 0.0836 mmol), acetonitrile (5.20 mL, 0.0996 mol), acetic anhydride (8.68 μL, 0.092 mmol), N,N-diisopropylethylamine (36.4 μL, 0.209 mmol) and N,N-dimethylaminopyridine (0.0005 g, 0.004 mmol). The mixture was stirred overnight and the precipitate was filtered and washed with Et2O to give 0.028 g (53% yield) of product as a white solid.

Workup

filtrationthe precipitate was filtered
washwashed with Et2O

Sources & evidence

ORD record: ord-68189b8822ef4d358f1a137c8732b4ea
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664200B2

Reaction notes

Loading…