p-Toluenesulfonic acid → HCID 68556594, compound

HRID 420288Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:18]([F:33])[CH:17]=2)[CH2:11][S:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CO[C:37](OC)([CH3:39])[CH3:38].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:7]1[C@@H:8]2[C@H:13]([C@H:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:24])=[C:18]([F:33])[CH:17]=3)[CH2:11][S:10][CH2:9]2)[O:14][C:37]1([CH3:39])[CH3:38])=[O:34])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of [(3R*,4S*,5S*)-5-(4-benzyloxycarbonylamino-3-fluoro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester (50.5 g, 102.9 mmol) and acetone dimethylketal (263 mL, 2.06 mol) in CH2Cl2 (500 mL) was added p-TsOH (200 mg, 1 mmol) at 0-5° C. and the reaction mixture was stirred for 4 h at 25° C. The reaction mixture was washed with saturated NaHCO3 solution and water, dried over MgSO4, filtered and evaporated to dryness. The title compound obtained as a yellow oil was used as such in the next step: TLC (toluene-EtOAc 3:1) Rf=0.40; HPLC RtA=2.80 min; ESIMS [M−H]−=529; 1H NMR (400 MHz, CDCl3): δ 7.99 (m, 1H), 7.38 (m, 5H), 6.92 (m, 2H), 6.84 (s, 1H), 5.21 (s, 2H), 3.3-3.6 (m, 2H), 3.03 (m, 2H), 2.52 (m, 2H), 2.38 (dt, 1H), 2.34 (t, 1H), 2.20 (m, 1H), 1.58 (s, 3H), 1.52 (s, 3H), 1.43 (s, 9H).

Workup

washThe reaction mixture was washed with saturated NaHCO3 solution and water
dry with materialdried over MgSO4
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-fa8b927da31c4281a6191c399bbf7bdf
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093406B2

Reaction notes

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