HCID 71278244, compound → HCID 71278256, compound

HRID 1427403Notes

Reaction equation

C(OC(=O)NC1SC[C@@H]2C[C@H](CO)OC[C@]2(C2C=CC=CC=2F)N=1)(C)(C)C.[C:28]([O:32][C:33](=[O:55])[NH:34][C:35]1[S:36][CH2:37][C@@H:38]2[CH2:44][C@H:43]([CH2:45][F:46])[O:42][CH2:41][C@:39]2([C:47]2[CH:52]=[CH:51][C:50](F)=[CH:49][C:48]=2[F:54])[N:40]=1)([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33](=[O:55])[NH:34][C:35]1[S:36][CH2:37][C@@H:38]2[CH2:44][C@H:43]([CH2:45][F:46])[O:42][CH2:41][C@:39]2([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[F:54])[N:40]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

Reactant 2

HCID 71278244HCID 71278244, compound

HCID 71278246HCID 71278246, compound

Product 1

HCID 71278256HCID 71278256, compound

Procedure

Compound C26 was prepared from tert-butyl[(4aR,6R,8aS)-8a-(2-fluorophenyl)-6-(hydroxymethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate (C18) according to the general procedure for the synthesis of tert-butyl[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(fluoromethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate (C25) in Example 4, except that no chromatography was carried out on the crude product. Yield: 40 mg, 0.10 mmol, 100%. LCMS m/z 397.4 (M−1).

Sources & evidence

ORD record: ord-ab385e3243ba4e748c6293c7c1c209ef
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933221B2

Reaction notes

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