Water → HCID 10863545, compound

HRID 1984768Notes

Reaction equation

HRID 1984768 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH3:31])[CH2:12][O:11][S:10](=[O:13])[N:9]1[CH:14]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:32]>CC#N>[C:1]([O:5][C:6]([C:8]1([CH3:31])[CH2:12][O:11][S:10](=[O:32])(=[O:13])[N:9]1[CH:14]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 11134098HCID 11134098, compound

Product 1

HCID 10863545HCID 10863545, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the diastereomeric sulfamidites 13a (97 mg, 0.22 mmol) in 4 mL of CH3CN was cooled in an ice bath and treated successively with 1.1 eq of NaIO4 (51 mg), a catalytic amount of RuO2.H2O (˜1 mg) and 2.4 mL of H2O. After 5 minutes of stirring the ice bath was removed, and the reaction was continued for 20 minutes. The reaction mixture was diluted in 10 mL of EtOAc and washed with 10 mL of saturated NaHCO3 solution. The aqueous layer was extracted with 2×10 mL of EtOAc, and the combined organic layers were washed with 10 mL brine followed by usual work up. The crude product was purified by silica gel column chromatography (30% EtOAc in hexane) to provide the cyclic sulfamidate 14a as a light yellow solid (90 mg, 89%): mp 143.5-145 EC (EtOAc.hexane); 1H NMR (CDCl3) δ 1.29 (3H, s), 1.51 (9H, s), 3.77 (3H, s), 3.80 (3H, s), 4.16 (1H, d, J=8.8), 4.73 (1H, d, J=8.8), 5.98 (1H, s), 6.82-6.89 (4H, m), 7.38-7.44 (4H). Anal. (C23H29NO7S)C,H,N.

Workup

  1. customwas removed
  2. additionThe reaction mixture was diluted in 10 mL of EtOAc
  3. washwashed with 10 mL of saturated NaHCO3 solution
  4. extractionThe aqueous layer was extracted with 2×10 mL of EtOAc
  5. washthe combined organic layers were washed with 10 mL brine
  6. customThe crude product was purified by silica gel column chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-2cbef666fde74fac9cda17823f591ed9
Source dataset
uspto-grants-2009_06
Patent number
US07544715B2

Reaction notes

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