Hydrochloric Acid → HCID 86714053, compound

HRID 2206717Notes

Reaction equation

[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[C:35]([O:37]C)[C:34]([Cl:39])=[C:33]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=3)[CH:32]=2)[O:11][C@@H:10]1[CH2:50][O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CN(C=O)C>[Cl:39][C:34]1[C:33]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=2)=[CH:32][C:31]([C@H:12]2[C@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:10]([CH2:50][O:51][CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[O:11]2)=[CH:36][C:35]=1[OH:37]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of compound 76 (3.0 g, 3.82 mmol) in DMF (38 mL) was added NaSEt (1.1 g, 13.35 mmol) at 90° C. The mixture was stirred at 90° C. for 6 hours. To a mixture was added 1 N HCl (50 mL) and extracted EtOAc (200 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 77 (3.0 g).

Workup

additionwas added NaSEt (1.1 g, 13.35 mmol) at 90° C
extractionextracted EtOAc (200 mL)
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0f3cc04f451f4fc2b69353c57bcb4d2c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371303B2

Reaction notes

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