HCID 60139864, compound → HCID 60139805, compound

HRID 270522Notes

Reaction equation

HRID 270522 reaction equation
[Si]([O:18][C@@H:19]([CH3:46])[C:20]([N:22]1[N:26]=[C:25]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[F:34])[S:24][C@:23]1([CH2:41][O:42][CH2:43][O:44][CH3:45])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:21])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.F[C:48]1C=CC(F)=CC=1C1S[C@@](CO)(C2C=CC=CC=2)N(C(=O)[C@@H](OC)C)N=1>>[F:34][C:28]1[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=1[C:25]1[S:24][C@:23]([CH2:41][O:42][CH2:43][O:44][CH3:45])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:22]([C:20](=[O:21])[C@@H:19]([O:18][CH3:48])[CH3:46])[N:26]=1

Participants

3

Reactant 2

HCID 60139864HCID 60139864, compoundHCID 67214967HCID 67214967, compound

Product 1

HCID 60139805HCID 60139805, compound

Procedure

Prepared as previously described in Example 83 using (S)-2-(tert-butyldiphenylsilyloxy)-1-((S)-5-(2,5-difluorophenyl)-2-((methoxymethoxy)methyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-one from Step C. MS ESI (+) m/z 437 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.53 (m, 1H), 7.43 (m, 2H), 7.37 (m, 2H), 7.31 (m, 1H), 7.11 (m, 2H), 4.76 (m, 4H), 4.47 (d, 1H, J=10 Hz), 3.41 (s, 3H), 3.35 (s, 3H), 1.47 (d, 3H, J=7 Hz). Stereochemistry was assigned by inference from (S)-1-((R)-5-(2,5-difluorophenyl)-2-(hydroxymethyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-659e9e3087c24e29af35a591eed25006
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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