Lawesson's reagent → (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)-1,3,4-thiadiazol-2-yl)phenyl)propanoate

HRID 1775822Notes

Reaction equation

COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:10]2)=CC=1.[C:23]([C:27]1[CH:67]=[CH:66][C:30]([C:31]([NH:33][C@@H:34]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([NH:48][NH:49][C:50](=O)[C:51]3[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])=[CH:53][CH:52]=3)=O)=[CH:42][CH:41]=2)[C:35]([O:37][CH3:38])=[O:36])=[O:32])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([C:27]1[CH:67]=[CH:66][C:30]([C:31]([NH:33][C@@H:34]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]3[S:10][C:50]([C:51]4[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])=[CH:53][CH:52]=4)=[N:49][N:48]=3)=[CH:42][CH:41]=2)[C:35]([O:37][CH3:38])=[O:36])=[O:32])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 65 °C

Procedure

Prepared using INT-3: To a stirring solution of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (65.7 mg, 0.16 mmol) in THF (3 mL) was added (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(2-(4-(heptyloxy)benzoyl)hydrazinecarbonyl)phenyl)propanoate INT-3 (100.0 mg, 0.16 mmol) and the mixture heated to 65° C. After 1 h, the reaction mixture was concentrated and purified by column chromatography (10-100% EA in iso-hexanes) to afford 37.0 mg (29%) of (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)-1,3,4-thiadiazol-2-yl)phenyl)propanoate as a yellow solid. LCMS-ESI (m/z) calculated for C36H43N3O4S: 613.8; no ion observed, tR=3.31 min. (Method 4).

Workup

customPrepared
concentrationthe reaction mixture was concentrated
custompurified by column chromatography (10-100% EA in iso-hexanes)

Sources & evidence

ORD record: ord-f75eff59dbc94d909cbd8d03b016516d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260427B2

Reaction notes

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