Potassium Carbonate → HCID 11552805, compound

HRID 1794589Notes

Reaction equation

HRID 1794589 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[C:13]([CH3:15])([CH3:14])[S:12][CH2:11][CH2:10][N:9]1[S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25]C(=O)C)=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCCC>CO.O>[C:1]([O:5][C:6]([C@H:8]1[C:13]([CH3:15])([CH3:14])[S:12][CH2:11][CH2:10][N:9]1[S:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 69667003HCID 69667003, compound

Product 1

HCID 11552805HCID 11552805, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
28 °C

Procedure

A suspension of 4-(4-Acetoxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3(S)-carboxylic acid tert-butyl ester (1 kg, 2.33 mol) and potassium carbonate (354 g, 2.56 mol) in methanol (5 L) and water (500 mL) was stirred at ambient temperature (internal temp=28° C.) for 3.5 hours. The reaction was determined to be complete by TLC (1:1 EtOAc/hexane). The solvent was removed under vacuum. The residue was diluted with water (5 L) and the pH adjusted to 2 with 12 M hydrochloric acid (˜400 mL). The resulting solid was collected by filtration, washed with water, and dried in a vacuum oven at 60° C. to give 879 g of 4-(4hydroxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3(S)-carboxylic acid tert-butyl ester (97% yield). This compound had the following properties: m.p. 171.3° C.; [α]D25=−1.97° (c 0.61, MeOH); IR (KBr): 3376, 2978, 2936, 1734, 1601, 1587, 1369, 1325 cm−1; 1H NMR (300 MHz, CDCl3): δ 7.61 (d, J=8.8 Hz, 2H, ArH), 6.86 (d, J=8.8 Hz, 2H, ArH), 4.30 (s, 1H, CαH), 4.04 (m, 1H), 3.85 (dt, J=12.7 and 2.6 Hz, 1H), 3.11 (dt, J=13.6 and 4.1 Hz, 1H), 2.43 (br d, J=13.6 Hz, 1H), 1.60 (s, 3H, CH3), 1.33 (s, 3H, CH3), 1.31 (s, 9H, But); 13C NMR (75 MHz, CDCl3): δ168.1 (C═O), 160.3, 131.8, 129.7 (×2), 116.2 (×2), 82.8, 63.9, 41.5, 40.6, 29.1, 28.3 (×3), 27.8, 25.0; Anal. Calculated for C17H25NO5S2+0.5% water (Karl Fisher analysis): C, 52.69; H, 6.50; N, 3.61; S, 16.55. Found: C, 52.73; H, 6.54; N, 3.64; S, 16.45.

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe residue was diluted with water (5 L)
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-529aea838aac4165ab21499cc4d90e19
Source dataset
uspto-grants-2006_04
Patent number
US07022846B2

Reaction notes

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