HCID 89455778, compound → HCID 71508338, compound

HRID 1776459Notes

Reaction equation

C(OC([N:8]([C:13]1[CH:51]=[CH:50][C:16]([C:17]([NH:19][CH2:20][C:21]([O:23][C@H:24]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:44])[F:43])=[C:37]([O:45][CH2:46][CH:47]3[CH2:49][CH2:48]3)[CH:36]=2)[CH2:25][C:26]2[C:31]([Cl:32])=[CH:30][N+:29]([O-:33])=[CH:28][C:27]=2[Cl:34])=[O:22])=[O:18])=[CH:15][C:14]=1[O:52][CH2:53][CH:54]1[CH2:56][CH2:55]1)[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C>Cl.CCOC(C)=O>[Cl:34][C:27]1[CH:28]=[N+:29]([O-:33])[CH:30]=[C:31]([Cl:32])[C:26]=1[CH2:25][C@@H:24]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:43])[F:44])=[C:37]([O:45][CH2:46][CH:47]2[CH2:49][CH2:48]2)[CH:36]=1)[O:23][C:21](=[O:22])[CH2:20][NH:19][C:17](=[O:18])[C:16]1[CH:50]=[CH:51][C:13]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:14]([O:52][CH2:53][CH:54]2[CH2:55][CH2:56]2)[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-4-(2-(2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzamido)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (180 mg, 0.2 mmol) was dissolved in HCl 4M in EtOAc and stirred overnight at 0° C. The solvent was evaporated under vacuum, and the crude product was purified by Preparative reverse-phase HPLC to give 12 mg of the final product (Yield: 8%).

Workup

customThe solvent was evaporated under vacuum
customthe crude product was purified by Preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-1e517763340a42cd88a7dceed2c9e99b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265768B2

Reaction notes

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