Hydrochloric Acid → HCID 86587923, compound

HRID 488530Notes

Reaction equation

[NH2:1][C:2]([O:4][C@@H:5]([C@@H:48]([CH3:53])/[CH:49]=[CH:50]\[CH:51]=[CH2:52])[C@@H:6]([CH3:47])[C@H:7]([O:39][Si](C(C)(C)C)(C)C)[C@@H:8]([CH3:38])[CH2:9]/[C:10](/[CH3:37])=[CH:11]\[C@H:12]([CH3:36])[C@@H:13]([O:28][Si](C(C)(C)C)(C)C)[C@@H:14]([CH3:27])/[CH:15]=[CH:16]\[C:17]([N:19]([CH3:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18])=[O:3].Cl.C([O-])(O)=O.[Na+]>CO>[NH2:1][C:2]([O:4][C@@H:5]([C@@H:48]([CH3:53])/[CH:49]=[CH:50]\[CH:51]=[CH2:52])[C@@H:6]([CH3:47])[C@H:7]([OH:39])[C@@H:8]([CH3:38])[CH2:9]/[C:10](/[CH3:37])=[CH:11]\[CH:12]([CH3:36])[CH:13]([OH:28])[CH:14]([CH3:27])/[CH:15]=[CH:16]\[C:17]([N:19]([CH3:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:18])=[O:3]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of (2Z,4S,5S,6S,7Z,10S,11R,12R,13S,14S,15Z)-13-[(aminocarbonyl)oxy]-5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-N,4,6,8,10,12,14-heptamethyl-N-phenyl-2,7,15,17-octadecatetraenamide (70 mg, 0.091 mmol, 1 eq) in MeOH (10 mL) is added a MeOH solution of HCl (15.5 mL, 15 mL MeOH+0.5 mL 12N HCl). The resulting solution is stirred at 23° C. (36 hours). The pH is adjusted to 8 by the addition of solid NaHCO3 at 0° C. The solution was dried in vacuo, the residue was dissolved in CH2Cl2 (10 mL) and filter through Celite. HPLC purification provided the desired compound (15.5 mg, 32%) as a white solid: [α]25D=+225.738° (c 0.25, CH2Cl2); HRMS ESI m/z 541.3588 (M+H+, C32H50O5N2 requires 541.3641).

Workup

customThe solution was dried in vacuo
dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
filtrationfilter through Celite
customHPLC purification

Sources & evidence

ORD record: ord-dc4099b4fbeb4724a87f9bd4440a5fd5
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972292B2

Reaction notes

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