Hydrochloric Acid → HCID 86681675, compound

HRID 571260Notes

Reaction equation

HRID 571260 reaction equation
C(OC([N:8]([C:13]1[CH:52]=[CH:51][C:16]2[N:17]([CH2:21][C:22]([O:24][C@H:25]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH:43]([F:45])[F:44])=[C:38]([O:46][CH2:47][CH:48]4[CH2:50][CH2:49]4)[CH:37]=3)[CH2:26][C:27]3[C:32]([Cl:33])=[CH:31][N+:30]([O-:34])=[CH:29][C:28]=3[Cl:35])=[O:23])[C:18](=[O:20])[O:19][C:15]=2[CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C.Cl.C1COCC1>C(Cl)Cl>[Cl:33][C:32]1[CH:31]=[N+:30]([O-:34])[CH:29]=[C:28]([Cl:35])[C:27]=1[CH2:26][C@@H:25]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH:43]([F:44])[F:45])=[C:38]([O:46][CH2:47][CH:48]2[CH2:50][CH2:49]2)[CH:37]=1)[O:24][C:22](=[O:23])[CH2:21][N:17]1[C:16]2[CH:51]=[CH:52][C:13]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[CH:14][C:15]=2[O:19][C:18]1=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 89511771HCID 89511771, compound

Product 1

HCID 86681675HCID 86681675, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(2-(2-(6-(N-(tert-butoxycarbonyl)methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.200 g, 0.254 mmol) in DCM (10 ml) cooled to 0° C., HCl 4M in THF (0.634 ml, 2.54 mmol) was added, and the mixture was warmed to room temperature and stirred for 48 hours. A white solid precipitated. The precipitate was collected by filtration and washed with DCM affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(6-(methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetoxy)ethyl)pyridine 1-oxide (0.140 g, 0.203 mmol, 80% yield). MS/ESI+ 688.1 [MH]+; [αD]=−31.04, c=0.46, MeOH; 1H NMR (300 MHz, DMSO-d6) δ ppm 9.66 (br. s., 1H), 8.43 (s, 2H), 7.25 (d, 1H), 7.19 (d, 1H), 7.15 (d, 1H), 7.08 (d, 1H), 7.05 (dd, 1H), 6.96 (dd, 1H), 7.07 (t, 1H), 6.04 (dd, 1H), 4.82 (d, 1H), 4.70 (d, 1H), 3.92 (d, 2H), 3.40 (dd, 1H), 3.22 (dd, 1H), 2.99 (s, 3H), 1.07-1.41 (m, 1H), 0.48-0.70 (m, 2H), 0.25-0.44 (m, 2H).

Workup

  1. customA white solid precipitated
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with DCM

Sources & evidence

ORD record
ord-5ac89a4473a14a9197493fdd211bb999
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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