Hydrochloric Acid → HCID 59267314, compound

HRID 1182694Notes

Reaction equation

[C:1]([NH:4][C@@H:5]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:6]([NH:8][C@@H:9]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:10]([NH:12][C@H:13]([B:19]1[O:23][C@@H]2C[C@@H]3C[C@H]([C@]2(C)[O:20]1)C3(C)C)[CH2:14][CH:15]1[CH2:18][CH2:17][CH2:16]1)=[O:11])=[O:7])(=[O:3])[CH3:2].CO.CCCCCC.Cl.CC(C)CB(O)O>>[C:1]([NH:4][C@@H:5]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:6]([NH:8][C@@H:9]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:10]([NH:12][C@H:13]([B:19]([OH:23])[OH:20])[CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18]1)=[O:11])=[O:7])(=[O:3])[CH3:2]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 8058Hexane

HCID 2734395(2-Methylpropyl)boronic acid

HCID 68526470HCID 68526470, compound

Product 1

HCID 59267314HCID 59267314, compoundYield 51%

Procedure

Into a 1-neck round-bottom flask was added (2S)-2-(acetylamino)-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 (24.8 mg, 0.0395 mmol), methanol (0.237 mL, 5.86 mmol), hexane (0.237 mL, 1.81 mmol), hydrochloric acid (0.0889 mmol, 0.0889 mmol) and 2-methylpropylboronic acid (8.65 mg, 0.0849 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was purified by preparative TLC in 10% MeOH/CH2Cl2 to give 9.90 mg (51% yield) of desired product as a white solid. 1H NMR (CD3OD, 300 MHz, δ): 7.32-7.12 (m, 10H); 4.74 (t, J=7.94 Hz, 1H); 4.26 (dd, J=5.49, 8.55 Hz, 1H); 3.14-3.05 (m, 2H); 2.66-2.55 (m, 2H); 2.48-2.41 (m, 1H); 2.19-2.05 (m, 1H); 2.04-1.89 (m, 8H); 1.89-1.69 (m, 3H); 1.58-1.36 (m, 3H); 1.33-1.22 (m, 1H).

Workup

customThe reaction mixture was purified by preparative TLC in 10% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-9dd5711ad72e4683897f4e12892f8380
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664200B2

Reaction notes

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