Potassium Hydroxide → HCID 86663490, compound

HRID 1399475Notes

Reaction equation

[OH-].[K+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]#[C:13][C:14]1[C:15]([O:51][CH2:52][CH2:53][CH2:54][S:55]([OH:58])(=[O:57])=[O:56])=[C:16]([C:21]([O:43][CH2:44][CH2:45][CH2:46][S:47]([OH:50])(=[O:49])=[O:48])=[C:22]([C:32]#[C:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:23]=1[O:24][CH2:25][CH2:26][CH2:27][S:28]([OH:31])(=[O:30])=[O:29])[C:17]([O:19]C)=[O:18])=[O:9])([CH3:6])([CH3:5])[CH3:4]>O>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]#[C:13][C:14]1[C:15]([O:51][CH2:52][CH2:53][CH2:54][S:55]([OH:58])(=[O:57])=[O:56])=[C:16]([C:21]([O:43][CH2:44][CH2:45][CH2:46][S:47]([OH:50])(=[O:49])=[O:48])=[C:22]([C:32]#[C:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[C:23]=1[O:24][CH2:25][CH2:26][CH2:27][S:28]([OH:31])(=[O:29])=[O:30])[C:17]([OH:19])=[O:18])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

Conditions

Temperature: 55 °C

Procedure

Aq. KOH solution (1 M, 793 μl, 0.793 mmol, 5.00 eq) was added to a solution of 8d (184 mg, 0.159 mmol, 1.00 eq) in water (1.00 ml) and the mixture was heated to 55° C. for 15 h. The product was purified by reverse phase HPLC (Waters Xterra C18 RP 30×100 column, 0-27% AcN in 0.1 M TEAB, Akta Purifier) to give 8f (122 mg, 67% yield). LCMS: Calculated Mass 842.2, Observed Mass 841.1 (M−).

Workup

customThe product was purified by reverse phase HPLC (Waters Xterra C18 RP 30×100 column, 0-27% AcN in 0.1 M TEAB, Akta Purifier)

Sources & evidence

ORD record: ord-f574507902574b55a43d06f2cfb606b0
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906612B2

Reaction notes

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