Hydrochloric Acid → (1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-5-(7-hydroxymethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one

HRID 421511Notes

Reaction equation

[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]([C:18]3[NH:23][C:22]4[S:24][CH:25]=[C:26]([CH2:27][O:28]COC)[C:21]=4[S:20](=[O:33])(=[O:32])[N:19]=3)=[C:14]([OH:34])[C@H:13]3[C@@H:8]2[C@H:9]2[CH2:35][C@@H:12]3[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]([C:18]3[NH:23][C:22]4[S:24][CH:25]=[C:26]([CH2:27][OH:28])[C:21]=4[S:20](=[O:32])(=[O:33])[N:19]=3)=[C:14]([OH:34])[C@H:13]3[C@@H:8]2[C@H:9]2[CH2:35][C@@H:12]3[CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-5-(7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one (0.42 g, 0.76 mmol) in dioxane (3 mL) was added a 4.0 M solution of hydrochloric acid in dioxane (9 mL). The reaction was stirred at 25° C. for 2 h before it was concentrated in vacuo to afford the crude product, (1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-5-(7-hydroxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-3-aza-tricyclo[6.2.1.02,7]undec-5-en-4-one (0.38 g, 0.76 mmol, 100%), which was used in the next step without further purification.

Workup

concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-5c3acfe3a6374252820b5e4012e1ad14
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097613B2

Reaction notes

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