Hydrochloric Acid → HCID 86601880, compound

HRID 915281Notes

Reaction equation

HRID 915281 reaction equation
[C:1]([N:4]([CH2:24][C@@H:25]1[O:29][C:28](=[O:30])[N:27]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][S:40](=[O:44])(=[O:43])[CH2:39][CH2:38]3)=[C:33]([F:45])[CH:32]=2)[CH2:26]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:23])[C@@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:12]([CH3:14])[CH3:13])=[O:6])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.C1COCC1.[ClH:59]>O1CCOCC1>[ClH:59].[C:1]([N:4]([CH2:24][C@@H:25]1[O:29][C:28](=[O:30])[N:27]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:38][CH2:39][S:40](=[O:43])(=[O:44])[CH2:41][CH2:42]3)=[C:33]([F:45])[CH:32]=2)[CH2:26]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:23])[C@@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:12]([CH3:13])[CH3:14])=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 8028TetrahydrofuranHCID 11204569HCID 11204569, compound

Product 1

HCID 86601880HCID 86601880, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following General procedure G, except that the entire reaction is performed at RT. 2(S)-tert-Butoxycarbonylamino-3-methyl-butyric acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamoyloxy)-methyl ester (12c) (0.40 g, 0.61 mmol), anisole (0.6 mL), THF (12 mL), and 4 M HCl in dioxane (4.6 mL) gave the title compound in 55% yield (0.20 g). 1H NMR (400 MHz, CD3OD): δ 7.51 (dd, 1H), 7.37 (t, 1H), 7.26 (dd, 1H), 6.06 (d, 1H), 6.01 (d, 1H), 4.87 (m, 1H), 4.20 (m, 2H), 4.10 (m, 2H), 3.84 (dd, 1H), 3.37 (m, 2H), 3.24 (tt, 1H), 3.12 (m, 2H), 2.54 (s, 3H), 2.36 (m, 3H), 2.17 (m, 2H), 1.10 (d, 3H), 1.09 (d, 3H). MS-APCI (m/z+): 558.

Workup

  1. customexcept that the entire reaction
  2. customis performed at RT

Sources & evidence

ORD record
ord-037b57207a884d93bcc11c5d15eb715e
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

Loading…