Methanol → HCID 67288325, compound

HRID 46210Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[C@H:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:14]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@H:13]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@@H:12]([CH2:40][O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:11]2)=[CH:6][C:5]=1[CH:49]([C:54]1[N:55]=[N:56][C:57]2[CH:63]=[C:62]([CH3:64])[CH:61]=[CH:60][C:58]=2[N:59]=1)C(OC)=O.C1COCC1.CO>C(Cl)Cl.O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[C@H:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:14]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@H:13]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C@@H:12]([CH2:40][O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:11]2)=[CH:6][C:5]=1[CH2:49][C:54]1[N:55]=[N:56][C:57]2[CH:63]=[C:62]([CH3:64])[CH:61]=[CH:60][C:58]=2[N:59]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydroxide (40 mg, 0.81 mmol) was added to methyl 2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-(7-methylbenzo[e][1,2,4]triazin-3-yl)acetate (compound 62, 228 mg, 0.27 mmol) in the mixture of THF, MeOH and water (9/1/1 ratio) at room temperature, and then the mixture was stirred at 70° C. for a 1 day until starting material was disappeared. After reaction complete, the solution was work-up with CH2Cl2. After evaporating the volatile solvent, silica gel column chromatography (Hx/EtOAc=⅓) gave the desired compound (115 mg, 73% yield) as light yellow oil.

Workup

customAfter reaction complete
customAfter evaporating the volatile solvent, silica gel column chromatography (Hx/EtOAc=⅓)

Sources & evidence

ORD record: ord-178beb9bdf794efaa15a8c3bcd569f8c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541380B2

Reaction notes

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